GB1326745A - Chromone-2-carboxylic acid derivatives - Google Patents
Chromone-2-carboxylic acid derivativesInfo
- Publication number
- GB1326745A GB1326745A GB2000270A GB1326745DA GB1326745A GB 1326745 A GB1326745 A GB 1326745A GB 2000270 A GB2000270 A GB 2000270A GB 1326745D A GB1326745D A GB 1326745DA GB 1326745 A GB1326745 A GB 1326745A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- group
- acetyl
- alkyl
- 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
Links
- RVMGXWBCQGAWBR-UHFFFAOYSA-N 4-oxo-1-benzopyran-2-carboxylic acid Chemical class C1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 RVMGXWBCQGAWBR-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- JEVXRPQNTBCCSP-UHFFFAOYSA-N 1-(2-hydroxy-4-methoxy-5-sulfanylphenyl)ethanone Chemical compound C(C)(=O)C=1C(=CC(=C(C1)S)OC)O JEVXRPQNTBCCSP-UHFFFAOYSA-N 0.000 abstract 1
- CGJLHSZYCSQTEL-UHFFFAOYSA-N 1-(2-hydroxy-4-sulfanylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(S)C=C1O CGJLHSZYCSQTEL-UHFFFAOYSA-N 0.000 abstract 1
- QQZFVONVJPXCSQ-UHFFFAOYSA-N 1-(4-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1O QQZFVONVJPXCSQ-UHFFFAOYSA-N 0.000 abstract 1
- DFEMEUCHUACQJW-UHFFFAOYSA-N 2-[4-(4-hydroxyphenoxy)phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC1=CC=C(O)C=C1 DFEMEUCHUACQJW-UHFFFAOYSA-N 0.000 abstract 1
- CODXUYXNVGWMGY-UHFFFAOYSA-N 2-amino-2-hydroxy-1-phenylethanone Chemical compound NC(O)C(=O)C1=CC=CC=C1 CODXUYXNVGWMGY-UHFFFAOYSA-N 0.000 abstract 1
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 abstract 1
- WUNJOAKAYNOOMW-UHFFFAOYSA-N 4-acetyl-3-hydroxybenzenesulfonyl chloride Chemical compound CC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1O WUNJOAKAYNOOMW-UHFFFAOYSA-N 0.000 abstract 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 abstract 1
- SSFLMWYMRFOSFY-UHFFFAOYSA-N 5-acetyl-4-hydroxy-2-methoxybenzenesulfonic acid Chemical compound COC1=CC(O)=C(C(C)=O)C=C1S(O)(=O)=O SSFLMWYMRFOSFY-UHFFFAOYSA-N 0.000 abstract 1
- GTUOXYACWOFHDM-UHFFFAOYSA-N 6-iodo-4-oxochromene-2-carboxylic acid Chemical compound IC1=CC=C2OC(C(=O)O)=CC(=O)C2=C1 GTUOXYACWOFHDM-UHFFFAOYSA-N 0.000 abstract 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 abstract 1
- 206010002198 Anaphylactic reaction Diseases 0.000 abstract 1
- NNPOMABWJFJPTQ-UHFFFAOYSA-N C(C)(=O)C=1C=C(OC2=CC=C(O/C(/C(=O)O)=CC(=O)O)C=C2)C=CC1O Chemical compound C(C)(=O)C=1C=C(OC2=CC=C(O/C(/C(=O)O)=CC(=O)O)C=C2)C=CC1O NNPOMABWJFJPTQ-UHFFFAOYSA-N 0.000 abstract 1
- ABEUECQUVRTQSC-UHFFFAOYSA-N COC(C(=CC(=O)OC)OC1=CC=C(C=C1)I)=O Chemical compound COC(C(=CC(=O)OC)OC1=CC=C(C=C1)I)=O ABEUECQUVRTQSC-UHFFFAOYSA-N 0.000 abstract 1
- 238000005618 Fries rearrangement reaction Methods 0.000 abstract 1
- UILPJVPSNHJFIK-UHFFFAOYSA-N Paeonol Chemical compound COC1=CC=C(C(C)=O)C(O)=C1 UILPJVPSNHJFIK-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000036783 anaphylactic response Effects 0.000 abstract 1
- 208000003455 anaphylaxis Diseases 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 208000006673 asthma Diseases 0.000 abstract 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 abstract 1
- 150000004777 chromones Chemical class 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 150000002688 maleic acid derivatives Chemical class 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/24—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/54—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition of compounds containing doubly bound oxygen atoms, e.g. esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1326745 Chromone-2-carboxylic acid derivatives FISONS Ltd 19 April 1971 [25 April 1970] 20002/70 Heading C2C Novel compounds of the Formula I in which P, Q, T, P<SP>1</SP>, Q<SP>1</SP> and T<SP>1</SP> may be the same or different and may be H or substituents other than H, R<SP>1</SP> is H or substituted or unsubstituted C 1-10 alkyl or alkoxy groups or a substituted or unsubstituted aryl group, R<SP>12</SP> is H, -COCH 2 R<SP>1</SP>, alkyl or an allyl-alkyl group of up to 6C, X is a carbon-carbon bond or a single atom which may carry substituents not forming part of the linkage between the two benzene nuclei, and W is H or -COCH 2 R<SP>1</SP>, and salts, esters or amides thereof may be obtained by (a) reacting a compound of Formula II with a compound of Formula III in which L<SP>1</SP> is a good leaving group or a group -X<SP>1</SP>Y, Y being H or alkali metal, R is H or, together with the OOC group, forms an ester, L<SP>2</SP> is a good leaving group when L<SP>1</SP> is -X<SP>1</SP>Y, and a group -X<SP>1</SP>Y when L<SP>1</SP> is a good leaving group, and X<SP>1</SP> denotes -S- or -O-, (b) by cyclization of groups A<SP>1</SP> and A<SP>2</SP> in a compound of Formula VI where A<SP>1</SP> and A<SP>2</SP> represent pairs of groups (i) -COOHR<SP>1</SP>COCOR<SP>6</SP> and -OM, or (ii) -H- and -OC(COOM)=CR<SP>1</SP>-COOM, in which R<SP>6</SP> is an -OM group or a group convertible thereto, M is H or an alkali metal; (c) (i) subjecting to a Fries rearrangement a compound of Formula Id or (ii) opening the pyrone ring of a single chromone nucleus in a corresponding compound of Formula VIII under alkaline conditions; (d) by hydrolysing or oxidizing a compound of Formula I in which -COOH is replaced by D where D denotes a group which is hydrolysable or oxidizable to -COOH; (e) dehydrogenating a compound of Formula X (f) selectively hydrogenating a compound of I in which at least one of groups P to T<SP>1</SP> represents an alkenyl group; (g) subjecting to an elevated temperature a compound of Formula I in which R<SP>12</SP> is alkyl or allyl-alkyl and at least one of P<SP>1</SP> to T<SP>1</SP> is H; (h) by reacting an R ester of a compound of Formula I in which R<SP>12</SP> is H with a compound of formula R<SP>1</SP>CH 2 COOH or an anhydride or acid halide thereof; or (i) reacting a compound as used in (h) with R<SP>11</SP>Hal in which R<SP>11</SP> is an alkyl or allyl-alkyl group, and where desired or necessary converting the compound of Formula I into a pharmaceutically acceptable derivative thereof, or vice versa. The preparation of the following intermediates is also described: p-iodophenol reacts with acetylenedicarboxylic acid dimethyl ester to form 4-iodophenoxyfumaric acid dimethyl ester which is converted to the free acid which on heating with H 2 SO 4 yields 2-carboxy-6-iodochromone, the latter being esterified to the ethyl ester; 2-amino-2-hydroxyacetophenone is diazotized and reacted with potassium xanthate forming 2-hydroxy-5-mercaptoacetophenone; 4- acetyl-3-hydroxyaniline is diazotized and reacted with SO 2 forming 4-acetyl-3-hydroxybenzenesulphonyl chloride which is reduced to 4-acetyl-3- hydroxythiophenol and an Na salt is formed; 2-hydroxy-4-methoxy-acetophenone and chlorosulphonic acid yield 5-acetyl-4-hydroxy-2-methoxybenzenesulphonic acid, the K salt of which is reacted with POCl 3 to give the corresponding sulphonyl chloride which is then reduced to 5- acetyl - 4 - hydroxy - 2 - methoxy - thiophenol; 4 - (4 - hydroxyphenoxy)phenylacetate reacts with chlorobenzene forming 2-hydroxy-5-(4- hydroxyphenoxy)acetophenone which is reacted with dimethyl acetylene dicarboxylate to form 60% of 4-(3-acetyl-4-hydroxyphenoxy)phenoxy fumaric acid and 40% of the corresponding substituted maleic acid; 4,41-dihydroxydiphenylmethane reacts with acetic anhydride forming 4-acetoxy-4<SP>1</SP>-dihydroxydiphenyl methane (and also the diacetoxy compound) which rearranges in the presence of TiCl 4 to 3-acetyl-4,41-dihydroxydiphenylmethane. Pharmaceutical compositions useful in the treatment of disorders in which the slowreacting substance of anaphylaxis (SRS-A) is a factor, e.g. skin afflictions, hay fever, or asthma, comprise compounds of the Formula I with a pharmaceutically acceptable diluent or carrier in forms suitable for administration parenterally, orally, by inhalation or topically.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2000270 | 1970-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1326745A true GB1326745A (en) | 1973-08-15 |
Family
ID=10138712
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2000270A Expired GB1326745A (en) | 1970-04-25 | 1970-04-25 | Chromone-2-carboxylic acid derivatives |
Country Status (6)
| Country | Link |
|---|---|
| CH (5) | CH562238A5 (en) |
| DE (1) | DE2120443A1 (en) |
| FR (1) | FR2092089B1 (en) |
| GB (1) | GB1326745A (en) |
| IL (1) | IL36572A0 (en) |
| NL (1) | NL7105580A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1144905A (en) * | 1965-03-25 | 1969-03-12 | Fisons Pharmaceuticals Ltd | Substituted bis-(2-carboxy-chromonyl-oxy) derivatives and preparation and pharmaceutical compositions thereof |
| GB1204122A (en) * | 1966-09-19 | 1970-09-03 | Fisons Pharmaceuticals Ltd | Novel bis-phenyl derivatives and the preparation thereof |
-
1970
- 1970-04-25 GB GB2000270A patent/GB1326745A/en not_active Expired
-
1971
- 1971-04-08 IL IL36572A patent/IL36572A0/en unknown
- 1971-04-23 CH CH727873A patent/CH562238A5/xx not_active IP Right Cessation
- 1971-04-23 CH CH1453674A patent/CH562239A5/xx not_active IP Right Cessation
- 1971-04-23 CH CH728073A patent/CH559203A5/xx not_active IP Right Cessation
- 1971-04-23 NL NL7105580A patent/NL7105580A/xx unknown
- 1971-04-23 FR FR7114481A patent/FR2092089B1/fr not_active Expired
- 1971-04-23 CH CH727973A patent/CH559202A5/xx not_active IP Right Cessation
- 1971-04-23 CH CH595871A patent/CH552581A/en not_active IP Right Cessation
- 1971-04-26 DE DE19712120443 patent/DE2120443A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH559202A5 (en) | 1975-02-28 |
| IL36572A0 (en) | 1971-06-23 |
| FR2092089A1 (en) | 1972-01-21 |
| CH562239A5 (en) | 1975-05-30 |
| CH562238A5 (en) | 1975-05-30 |
| CH552581A (en) | 1974-08-15 |
| NL7105580A (en) | 1971-10-27 |
| DE2120443A1 (en) | 1971-11-11 |
| FR2092089B1 (en) | 1974-11-15 |
| CH559203A5 (en) | 1975-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |