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US3926991A - Process for producing quinoxaline-di-N-oxides - Google Patents

Process for producing quinoxaline-di-N-oxides Download PDF

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Publication number
US3926991A
US3926991A US338906A US33890673A US3926991A US 3926991 A US3926991 A US 3926991A US 338906 A US338906 A US 338906A US 33890673 A US33890673 A US 33890673A US 3926991 A US3926991 A US 3926991A
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US
United States
Prior art keywords
acid
carbazate
reaction
methyl
oxidizing agent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US338906A
Inventor
Donald E Kuhla
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pfizer Corp Belgium
Pfizer Corp SRL
Original Assignee
Pfizer Corp Belgium
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pfizer Corp Belgium filed Critical Pfizer Corp Belgium
Priority to US338906A priority Critical patent/US3926991A/en
Priority to IE197/74A priority patent/IE39170B1/en
Priority to ZA740745A priority patent/ZA74745B/en
Priority to SE7401528A priority patent/SE420603B/en
Priority to NL7401966A priority patent/NL7401966A/xx
Priority to FI490/74A priority patent/FI59404C/en
Priority to YU00439/74A priority patent/YU39150B/en
Priority to IT48504/74A priority patent/IT1056054B/en
Priority to JP49019992A priority patent/JPS5024282A/ja
Priority to DK92574AA priority patent/DK138945B/en
Priority to ES423464A priority patent/ES423464A1/en
Priority to CH254874A priority patent/CH580096A5/xx
Priority to LU69471A priority patent/LU69471A1/xx
Priority to FR7406155A priority patent/FR2220524B1/fr
Priority to AR252487A priority patent/AR200516A1/en
Priority to HUPI408A priority patent/HU170488B/hu
Priority to CS7400001493A priority patent/CS180003B2/en
Priority to SU2002363A priority patent/SU539527A3/en
Priority to PL1974169209A priority patent/PL94858B1/pl
Priority to CA194,053A priority patent/CA982584A/en
Priority to GB1014974A priority patent/GB1459561A/en
Priority to US05/597,209 priority patent/US4006142A/en
Application granted granted Critical
Publication of US3926991A publication Critical patent/US3926991A/en
Priority to HK471/77A priority patent/HK47177A/en
Priority to MY13/78A priority patent/MY7800013A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
    • C07D241/52—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring

Definitions

  • oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide.
  • the present invention discloses a process for the preparation of methyl 3-( 2-quinoxalinylmethylene)carbazate N ,N -dioxide which comprises contacting methyl 3-(2-quinoxalinylmethylene)carbazate with at least about 2 equivalents of oxidizing agent in a reaction inert solvent at a temperature of from about C. up to 100C. until the reaction is substantially complete, said oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, mchloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide, and recovery of the product.
  • a catalyst is usually employed.
  • Suitable catalysts are tungstic acid, sodium tungstate, sodium vanadate, sodium molybdate, potassium tungstate, potassium molybdate, vanadium pentaoxide, zirconium dioxide, tungsten trioxide or molybdenum trioxide.
  • a particularly preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is peracetic acid and said solvent is acetic acid, since both the reagent and solvent are inexpensive.
  • a second preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is m-chloroperbenzoic acid and said solvent is chloroform.
  • reaction tem perature is preferably maintained at less than 50C.
  • the new reaction of the present invention is carried out in a reaction-inert solvent.
  • An inert solvent for purposes of this invention contemplates any solvent which allows solubilization of the reactants and is free of ad.- verse effect on the reagents and products under the conditions employed.
  • Two preferred types include organic acids, such as acetic acid, and halogenated solvents, such as chloroform and methylene chloride. In some cases water may be employed. However, any solvent possessing the qualities set forth above will be satisfactory.
  • the temperature at which the reaction is performed may vary from C. to about 100C. and for the most part the optimum temperature will vary with the choice of oxidizing agent. Depending upon the particular oxidizing agent and temperature, the reaction time can vary from a few minutes to as long as 24 hours. Generally, to ensure complete reaction the relatively long time periods are preferred. Optimum reaction conditions are readily determined by experiment.
  • the proportion of oxidizing agent relative to the starting carbazate may vary widely butfor efficient conversion at least about two equivalents of oxidizing agent per mole ofcarbanate are preferred.
  • the product is a crystalline substance which precipitates from the reaction mixture. It is collected by suit- .able means and dried.
  • the valuable product of this invention exhibits activity as urinary tract systemic anti-infective in animals, includingman, against a wide :variety of microorganisms including Gram positive and Gram-negative bacteria. It is especially valuable against Gram negative infection both invitro and in vivo.
  • poultry chickens, ducks, turkeys
  • the beneficial effects in growth rate and feed efficiency are over and above what is normally obtained with complete nutritious diets containing all the nutrients, vitamins, minerals and other factors known to be required for the maximum healthy growth of such animals.
  • the animals thus attain market size sooner and on less feed.
  • feed compositions have been found to be particularly valuable and outstanding in the case of such animals as poultry, rats, hogs, swine, lambs, cattle, and the like. In some instances the degree of response may vary with respect to the sex of the animals.
  • the products may, of course, be administered in one component of the feed or they may be blended uniformly throughout a mixed feed; alternatively as noted above, they may be administered in an equivalent amount via the animalss water ration. It should be noted that a variety of feed components may be of use in the nutritionally balanced feeds.
  • reaction mixture is allowed to stand for 12 hours and then diluted with water.
  • the solid which precipitates is collected, washed with water and dried to give crystalline methyl 3-(2-quinoxalinylmethylene)carbazate N ,N -dioxide.
  • EXAMPLE lll A mixture of methyl 3-( 2-quinoxalinylmethylene)- carbazate (23.0 g, 0.1 mole), tungstic acid (2.5 g) and 30 ml of t-butanol is heated to 6065. An aqueous solution of 30 percent hydrogen peroxide (30 ml) is solvent is acetic acid.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Luminescent Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The novel process for the preparation of methyl 3-(2quinoxalinylmethylene)carbazate N1, N4-dioxide which comprises contacting methyl 3-(2-quinoxalinylmethylene)carbazate with oxidizing agent in reaction-inert solvent at a temperature of from about 20*C. up to 100*C. until reaction is substantially complete, said oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide.

Description

United States Patent [191 Kuhla 5] Dec. 16, 1975 PROCESS FOR PRODUCING 3,720,673 3/1973 Bowie 260/250 QN QUINOXALINEDLNOXIDES 3,819,616 6/1974 Seng et at, 260/250 0 [75] Inventor: Donald E. Kuhla, Gales Ferry,
Conn.
[73] Assignee: Pfizer Inc., New York, NY.
[22] Filed: Mar. 7, 1973 [21] Appl. No.: 338,906
[52] US. Cl 260/250 Q; 424/250 [51] Int. Cl. C07D 241/36 [58] Field of Search 260/250 Q, 250 ON [56] References Cited UNITED STATES PATENTS 2,545,786 3/l95l Landquist 260/250 QN 2,626,259 4/l974 Landquist 260/250 QN Primary ExaminerRichard J Gallagher Assistant ExaminerDavid E, Wheeler Attorney, Agent, or Firm-Connolly and Hutz 57 ABSTRACT The novel process for the preparation of methyl 3-(2- quinoxalinylmethylene)carbazate N, N -dioxide which comprises contacting methyl 3-(2- quinoxalinylmethylene)carbazate with oxidizing agent in reaction-inert solvent at a temperature of from about 20C. up to 100C. until reaction is substantially complete, said oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide.
2 Claims, No Drawings PROCESS FOR PRODUCING Umox LmE-m-N-oxmizs ,BACKGROQ DQF THE INVENTION mals. (Australian Vet. 1.48,,No. 579, (1972) 21I1d Rec. Med. Vet. ecole Alfort. 148 No. 3 365-73 (1972)). l
SUMMARY OF THE INVENTION Accordingly the present invention discloses a process for the preparation of methyl 3-( 2-quinoxalinylmethylene)carbazate N ,N -dioxide which comprises contacting methyl 3-(2-quinoxalinylmethylene)carbazate with at least about 2 equivalents of oxidizing agent in a reaction inert solvent at a temperature of from about C. up to 100C. until the reaction is substantially complete, said oxidizing agent being selected from the group consisting of peracetic acid, perbenzoic acid, mchloroperbenzoic acid, perphthalic acid, performic acid, trifluoroperacetic acid and hydrogen peroxide, and recovery of the product. In the case of hydrogen peroxide a catalyst is usually employed. Suitable catalysts are tungstic acid, sodium tungstate, sodium vanadate, sodium molybdate, potassium tungstate, potassium molybdate, vanadium pentaoxide, zirconium dioxide, tungsten trioxide or molybdenum trioxide.
A particularly preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is peracetic acid and said solvent is acetic acid, since both the reagent and solvent are inexpensive.
A second preferred embodiment of the herein described invention concerns the above process wherein said oxidizing agent is m-chloroperbenzoic acid and said solvent is chloroform. P
In both of the above embodiments the reaction tem perature is preferably maintained at less than 50C.
The new reaction of the present invention is carried out in a reaction-inert solvent. An inert solvent for purposes of this invention contemplates any solvent which allows solubilization of the reactants and is free of ad.- verse effect on the reagents and products under the conditions employed. Two preferred types include organic acids, such as acetic acid, and halogenated solvents, such as chloroform and methylene chloride. In some cases water may be employed. However, any solvent possessing the qualities set forth above will be satisfactory. The temperature at which the reaction is performed may vary from C. to about 100C. and for the most part the optimum temperature will vary with the choice of oxidizing agent. Depending upon the particular oxidizing agent and temperature, the reaction time can vary from a few minutes to as long as 24 hours. Generally, to ensure complete reaction the relatively long time periods are preferred. Optimum reaction conditions are readily determined by experiment.
The proportion of oxidizing agent relative to the starting carbazate may vary widely butfor efficient conversion at least about two equivalents of oxidizing agent per mole ofcar bazate are preferred.
The product is a crystalline substance which precipitates from the reaction mixture. It is collected by suit- .able means and dried. F
- The valuable product of this invention exhibits activity as urinary tract systemic anti-infective in animals, includingman, against a wide :variety of microorganisms including Gram positive and Gram-negative bacteria. It is especially valuable against Gram negative infection both invitro and in vivo.
Further, the addition of a low level of the herein described Schiff base to the diet of animals, both ruminant and non-ruminant, such that these animals receive the product over an extended period of time, at a level of from about 0.04 mg./kg. to about 10 mg./kg. of body weight per day, especially over a major portion of their active growth period, results in an acceleration of the rate of growth and improved feed efficiency. Included in these two classes of animals are poultry (chickens, ducks, turkeys), cattle, sheep, dogs, cats, swine, rats, mice, horses, goats, mules, rabbits, mink, etc. The beneficial effects in growth rate and feed efficiency are over and above what is normally obtained with complete nutritious diets containing all the nutrients, vitamins, minerals and other factors known to be required for the maximum healthy growth of such animals. The animals thus attain market size sooner and on less feed.
These feed compositions have been found to be particularly valuable and outstanding in the case of such animals as poultry, rats, hogs, swine, lambs, cattle, and the like. In some instances the degree of response may vary with respect to the sex of the animals. The products, may, of course, be administered in one component of the feed or they may be blended uniformly throughout a mixed feed; alternatively as noted above, they may be administered in an equivalent amount via the animalss water ration. It should be noted that a variety of feed components may be of use in the nutritionally balanced feeds.
PREPARATION I A solution of 14.0 g (0.0886 mole) of 2-quinoxalinecarboxaldehyde (prepared by the method of Landquist and Silk, J. Chem. Soc. 1956, 2052), 100 ml of ethanol and 14.0 g (0.156 mole) of methylcarbazate is heated to reflux on a steam bath and is then allowed to stand at room temperature overnight/The product, methyl 3-(2-quinoxalinylmethylene)carbazate, crystallizes: yield 14.0 g (69 percent); m.p. 242244.
EXAMPLE I To a solution of methyl 3-(2-quinoxalinylmethylene)carbazate (46 g, 0.20 mole) in glacial acetic acid (200 ml) is added, in a dropwise manner, 40 percent peracetic acid (76 g, 0.40 mole) with the rate of addition such to maintain the temperature below about 50C.
The reaction mixture is allowed to stand for 12 hours and then diluted with water. The solid which precipitates is collected, washed with water and dried to give crystalline methyl 3-(2-quinoxalinylmethylene)carbazate N ,N -dioxide.
EXAMPLE II To a solution of methyl 3-(2-quinoxalinylmethylene)carbazate (46 g, 0.20 mole) in chloroform (300 ml) is added a solution of percent m- 3 chloroperbenzoic acid (82 g, 0.40 mole) in chloroform (300 ml). The reaction temperature is maintained below 50C. by adjusting the rate of addition and using external cooling.
After stirring 24 hours, the mixture is filtered and the solid slurried with excess aqueous sodium bicarbonate to remove m-chlorobenzoic acid. The slurry is filtered and the solid washed with water and dried to give methyl 3-(2-quinoxalinylmethylene)carbazate N,N- dioxide as a crystalline solid.
EXAMPLE lll A mixture of methyl 3-( 2-quinoxalinylmethylene)- carbazate (23.0 g, 0.1 mole), tungstic acid (2.5 g) and 30 ml of t-butanol is heated to 6065. An aqueous solution of 30 percent hydrogen peroxide (30 ml) is solvent is acetic acid.

Claims (2)

1. A PROCESS FOR THE PREPARATION OF METHYL-3-(2-QUINOXALINYLMETHYLENE)CARBAZATE-N1,N4-DIOXIDE WHICH COMPRISES THE STEP OF REACTING METHYL-3-(2-QUINOXALINYL METHYLENE)CARBAZATE WITH ABOUT TWO EQUIVALENTS OF PERACETIC ACID IN A REACTION INERT SOLVENT AT A TEMPERATURE OF FROM ABOUT 20* UP TO 100*C. UNTIL REACTION IS SUBSTANTIALLY COMPLETE.
2. The process of claim 1 wherein said reaction inert solvent is acetic acid.
US338906A 1973-03-07 1973-03-07 Process for producing quinoxaline-di-N-oxides Expired - Lifetime US3926991A (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
US338906A US3926991A (en) 1973-03-07 1973-03-07 Process for producing quinoxaline-di-N-oxides
IE197/74A IE39170B1 (en) 1973-03-07 1974-02-04 Process for producing a quinoxaline -n1 n4 - dioxide derivative
ZA740745A ZA74745B (en) 1973-03-07 1974-02-05 Carbacox from 2-quinoxaline,carboxaldehyde methyl carbazate
SE7401528A SE420603B (en) 1973-03-07 1974-02-05 PROCEDURE FOR THE PREPARATION OF METHYL-3- (2-CHINOXOLINYLMETHYL) -CARBAZATE-N? 721, N? 724-DIOXIDE
NL7401966A NL7401966A (en) 1973-03-07 1974-02-13
FI490/74A FI59404C (en) 1973-03-07 1974-02-20 PROCEDURE FOR FRAMSTATION OF METHYL-3- (2-QUINOXALYNYLMETHYLENE) CARBACATE-N1, N4-DIOXIDE
YU00439/74A YU39150B (en) 1973-03-07 1974-02-20 Process for obtaining methyl-3(2-quinoxalinyl-methylene carbazate n1,n4-dioxides
IT48504/74A IT1056054B (en) 1973-03-07 1974-02-20 PROCESS FOR THE PREPARATION OF MITIL 3 (2 KINOXALYL METALEN) CATALAZED IN THE N 4 DIOXIDE
DK92574AA DK138945B (en) 1973-03-07 1974-02-21 Process for the preparation of methyl 3- (2-quinoxalinylmethylene) carbazate N1, N4 dioxide.
ES423464A ES423464A1 (en) 1973-03-07 1974-02-21 A PROCEDURE FOR THE PREPARATION OF N ', N'-DIOXIDE OF METHYL 3- (2-QUINOXALINYL METHYLENE) CARBAZATE.
JP49019992A JPS5024282A (en) 1973-03-07 1974-02-21
LU69471A LU69471A1 (en) 1973-03-07 1974-02-22
CH254874A CH580096A5 (en) 1973-03-07 1974-02-22
FR7406155A FR2220524B1 (en) 1973-03-07 1974-02-22
AR252487A AR200516A1 (en) 1973-03-07 1974-02-22 PROCEDURE FOR PREPARING 3- (2-QUINOXALINYL METHYLENE) METHYL CARBAZATE N1, N4-DIOXIDE
HUPI408A HU170488B (en) 1973-03-07 1974-02-28
CS7400001493A CS180003B2 (en) 1973-03-07 1974-02-28 Method for production of n1,n4-dioxide of methyl-3/2-chinoxalinylmethylene/carbazate
PL1974169209A PL94858B1 (en) 1973-03-07 1974-03-01
SU2002363A SU539527A3 (en) 1973-03-07 1974-03-01 The method of obtaining 1-4-methyl-3- (2-quinoxalinylmethylene) carbazate
CA194,053A CA982584A (en) 1973-03-07 1974-03-05 Carbadox from 2-quinoxaline, carboxaldehyde methyl carbazate
GB1014974A GB1459561A (en) 1973-03-07 1974-03-06 Process for producing a quinoxaline-di-n-oxide derivative
US05/597,209 US4006142A (en) 1973-03-07 1975-07-18 Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide
HK471/77A HK47177A (en) 1973-03-07 1977-09-15 Process for producing a quinoxaline-di-n-oxide derivative
MY13/78A MY7800013A (en) 1973-03-07 1978-12-30 Process for producing a quinoxaline d1-n-oxide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US338906A US3926991A (en) 1973-03-07 1973-03-07 Process for producing quinoxaline-di-N-oxides

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/597,209 Division US4006142A (en) 1973-03-07 1975-07-18 Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide

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US3926991A true US3926991A (en) 1975-12-16

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US338906A Expired - Lifetime US3926991A (en) 1973-03-07 1973-03-07 Process for producing quinoxaline-di-N-oxides

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US (1) US3926991A (en)
JP (1) JPS5024282A (en)
AR (1) AR200516A1 (en)
CA (1) CA982584A (en)
CH (1) CH580096A5 (en)
CS (1) CS180003B2 (en)
DK (1) DK138945B (en)
ES (1) ES423464A1 (en)
FI (1) FI59404C (en)
FR (1) FR2220524B1 (en)
GB (1) GB1459561A (en)
HK (1) HK47177A (en)
HU (1) HU170488B (en)
IE (1) IE39170B1 (en)
IT (1) IT1056054B (en)
LU (1) LU69471A1 (en)
MY (1) MY7800013A (en)
NL (1) NL7401966A (en)
PL (1) PL94858B1 (en)
SE (1) SE420603B (en)
SU (1) SU539527A3 (en)
YU (1) YU39150B (en)
ZA (1) ZA74745B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006142A (en) * 1973-03-07 1977-02-01 Pfizer Inc. Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide
US4935575A (en) * 1988-12-12 1990-06-19 Uop Process for the oligomerization of olefins and a catalyst thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4740652A (en) * 1985-05-23 1988-04-26 Uop Inc. Process for the oligomerization of olefins
US4737479A (en) * 1986-03-21 1988-04-12 Uop Inc. Process for the oligomerization of olefins and a catalyst thereof
US4737480A (en) * 1986-03-25 1988-04-12 Uop Inc. Process for the oligomerization of olefins and a catalyst thereof
US4795851A (en) * 1987-03-12 1989-01-03 Uop Inc. Process for the oligomerization of olefins and a catalyst thereof
US4795852A (en) * 1987-03-13 1989-01-03 Uop Inc. Process for the oligomerization of olefins and a catalyst thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2545786A (en) * 1951-03-20 S-methoxyquinoxaline-l
US2626259A (en) * 1953-01-20 Ffiii-ce
US3479354A (en) * 1967-03-21 1969-11-18 Ici Ltd Derivatives of 5-hydroxyquinoxaline-1,4-dioxide
US3720673A (en) * 1970-06-18 1973-03-13 Ici Ltd Process for the manufacture of quinoxaline 1,4-dioxides
US3819616A (en) * 1970-04-02 1974-06-25 Bayer Ag Imines/their preparation and their pharmaceutical use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA725675B (en) * 1971-06-21 1973-05-30 Ciba Geigy Ag New heterocyclic compounds

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2545786A (en) * 1951-03-20 S-methoxyquinoxaline-l
US2626259A (en) * 1953-01-20 Ffiii-ce
US3479354A (en) * 1967-03-21 1969-11-18 Ici Ltd Derivatives of 5-hydroxyquinoxaline-1,4-dioxide
US3819616A (en) * 1970-04-02 1974-06-25 Bayer Ag Imines/their preparation and their pharmaceutical use
US3720673A (en) * 1970-06-18 1973-03-13 Ici Ltd Process for the manufacture of quinoxaline 1,4-dioxides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4006142A (en) * 1973-03-07 1977-02-01 Pfizer Inc. Preparation of methyl-3-(2-quinoxalinylmethylene)carbazate-N1,N4 -dioxide
US4935575A (en) * 1988-12-12 1990-06-19 Uop Process for the oligomerization of olefins and a catalyst thereof

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HK47177A (en) 1977-09-23
YU43974A (en) 1982-06-30
YU39150B (en) 1984-06-30
FI59404B (en) 1981-04-30
AR200516A1 (en) 1974-11-15
GB1459561A (en) 1976-12-22
FR2220524B1 (en) 1977-03-04
JPS5024282A (en) 1975-03-15
IE39170L (en) 1974-09-07
LU69471A1 (en) 1974-09-25
CH580096A5 (en) 1976-09-30
IE39170B1 (en) 1978-08-16
IT1056054B (en) 1982-01-30
DK138945B (en) 1978-11-20
SE420603B (en) 1981-10-19
CA982584A (en) 1976-01-27
HU170488B (en) 1977-06-28
CS180003B2 (en) 1977-12-30
NL7401966A (en) 1974-09-10
SU539527A3 (en) 1976-12-15
ES423464A1 (en) 1976-05-01
FI59404C (en) 1981-08-10
ZA74745B (en) 1974-12-24
FR2220524A1 (en) 1974-10-04
PL94858B1 (en) 1977-09-30
DK138945C (en) 1979-05-07
MY7800013A (en) 1978-12-31

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