NL8004103A - Werkwijze ter bereiding van 1.2-dihydro 2-oxo 5-(pyridinyl)nicotinonitrilen. - Google Patents

Werkwijze ter bereiding van 1.2-dihydro 2-oxo 5-(pyridinyl)nicotinonitrilen. Download PDF

Info

Publication number: NL8004103A
Authority: NL; Netherlands
Prior art keywords: pyridinyl; oxo; dihydro; ethanol; acrolein
Prior art date: 1979-07-26

Application number

NL8004103A

Other languages

English (en)

Dutch (nl)

Original Assignee

Sterling Drug Inc

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.)

1979-07-26

Filing date

1980-07-16

Publication date

1981-01-28

1980-07-16 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1981-01-28 Publication of NL8004103A publication Critical patent/NL8004103A/nl

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 title 1
-1 4-pyridinyl Chemical group 0.000 claims description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
238000000034 method Methods 0.000 claims description 21
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
125000004076 pyridyl group Chemical group 0.000 claims description 17
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 16
CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 7
238000006243 chemical reaction Methods 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
NTHQYHTZRJMPFI-UHFFFAOYSA-N 2-oxo-5-pyridin-2-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CC=N1 NTHQYHTZRJMPFI-UHFFFAOYSA-N 0.000 claims description 3
SEQOYYYZFNJQSV-UHFFFAOYSA-N 2-oxo-5-pyridin-4-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=NC=C1 SEQOYYYZFNJQSV-UHFFFAOYSA-N 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 4
DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
PNAHPHGJXNKLNF-UHFFFAOYSA-N 3-(dimethylamino)-2-pyridin-4-ylprop-2-enal Chemical compound CN(C)C=C(C=O)C1=CC=NC=C1 PNAHPHGJXNKLNF-UHFFFAOYSA-N 0.000 description 2
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
235000005152 nicotinamide Nutrition 0.000 description 2
150000005480 nicotinamides Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
UAOTWASOGSHQAI-UHFFFAOYSA-N 2-methoxy-5-pyridin-4-ylpyridine-3-carbonitrile Chemical compound C1=C(C#N)C(OC)=NC=C1C1=CC=NC=C1 UAOTWASOGSHQAI-UHFFFAOYSA-N 0.000 description 1
KFPKURCPGZGYHR-UHFFFAOYSA-N 2-oxo-5-pyridin-3-yl-1h-pyridine-3-carbonitrile Chemical compound C1=C(C#N)C(=O)NC=C1C1=CC=CN=C1 KFPKURCPGZGYHR-UHFFFAOYSA-N 0.000 description 1
LSKDIEBKDGDGBL-UHFFFAOYSA-N 2-oxo-5-pyridin-4-yl-3H-pyridine-3-carbonitrile Chemical compound O=C1C(C#N)C=C(C=N1)C1=CC=NC=C1 LSKDIEBKDGDGBL-UHFFFAOYSA-N 0.000 description 1
OTIZLYDEBSAMGZ-UHFFFAOYSA-N 3-amino-5-pyridin-2-yl-1h-pyridin-2-one Chemical class N1C(=O)C(N)=CC(C=2N=CC=CC=2)=C1 OTIZLYDEBSAMGZ-UHFFFAOYSA-N 0.000 description 1
XPKCTVWRMHSHFC-UHFFFAOYSA-N 5-(2-methylpyridin-3-yl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=NC=CC=C1C1=CNC(=O)C(C#N)=C1 XPKCTVWRMHSHFC-UHFFFAOYSA-N 0.000 description 1
PNWCHLYSZPVAPM-UHFFFAOYSA-N 5-(3-ethylpyridin-4-yl)-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CCC1=CN=CC=C1C1=CNC(=O)C(C#N)=C1 PNWCHLYSZPVAPM-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000037230 mobility Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or 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 to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NL8004103A 1979-07-26 1980-07-16 Werkwijze ter bereiding van 1.2-dihydro 2-oxo 5-(pyridinyl)nicotinonitrilen. NL8004103A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/060,758 US4223149A (en)	1979-07-26	1979-07-26	Process for producing 3-cyano-5-(pyridinyl)-2(1H)-pyridinones
US6075879		1979-07-26

Publications (1)

Publication Number	Publication Date
NL8004103A true NL8004103A (nl)	1981-01-28

Family

ID=22031563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004103A NL8004103A (nl)	1979-07-26	1980-07-16	Werkwijze ter bereiding van 1.2-dihydro 2-oxo 5-(pyridinyl)nicotinonitrilen.

Country Status (15)

Country	Link
US (1)	US4223149A (de)
JP (1)	JPS5620573A (de)
AR (1)	AR226853A1 (de)
AT (1)	ATA363280A (de)
CA (1)	CA1132570A (de)
DK (1)	DK313580A (de)
ES (1)	ES8105995A1 (de)
FI (1)	FI802283A7 (de)
GR (1)	GR69739B (de)
LU (1)	LU82648A1 (de)
NL (1)	NL8004103A (de)
NO (1)	NO802137L (de)
PT (1)	PT71539A (de)
SE (1)	SE8005287L (de)
ZA (1)	ZA804171B (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4365065A (en) *	1979-11-26	1982-12-21	Sterling Drug Inc.	1-(Pyridinyl)-2-(dimethylamino)ethenyl lower-alkyl ketones
US4347363A (en) *	1981-09-17	1982-08-31	Sterling Drug Inc.	Process for preparing 1,2-dihydro-6-methyl-2-oxo-5-(pyridinyl)nicotinonitriles
US4432979A (en) *	1981-10-26	1984-02-21	William H. Rorer, Inc.	Pyridone compounds
US4413127A (en) *	1982-05-24	1983-11-01	Sterling Drug Inc.	Preparation of 1,2-dihydro-6-(lower alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles
US4469871A (en) *	1982-05-24	1984-09-04	Sterling Drug Inc.	Process for preparing 2-(lower-alkoxy)-1-(pyridinyl) ethenyl lower-alkyl ketones
NO163008C (no) *	1982-05-24	1990-03-21	Sterling Drug Inc	2-(laverealkoksy)-1-(pyridinyl)etenyl-lavere-alkylketon og fremgangsmaate for fremstilling av pyridinylnikotinderivater.
US4417054A (en) *	1982-05-24	1983-11-22	Sterling Drug Inc.	2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4004012A (en) *	1975-10-14	1977-01-18	Sterling Drug Inc.	3-Cyano-5-(pyridinyl)-2(1H)-pyridinones
US4072746A (en) *	1975-10-14	1978-02-07	Sterling Drug Inc.	3-Amino-5-(pyridinyl)-2(1H)-pyridinones

1979
- 1979-07-26 US US06/060,758 patent/US4223149A/en not_active Expired - Lifetime
1980
- 1980-01-28 GR GR62455A patent/GR69739B/el unknown
- 1980-07-02 AR AR281620A patent/AR226853A1/es active
- 1980-07-11 ZA ZA00804171A patent/ZA804171B/xx unknown
- 1980-07-11 AT AT0363280A patent/ATA363280A/de not_active IP Right Cessation
- 1980-07-11 PT PT71539A patent/PT71539A/pt unknown
- 1980-07-16 NO NO802137A patent/NO802137L/no unknown
- 1980-07-16 NL NL8004103A patent/NL8004103A/nl not_active Application Discontinuation
- 1980-07-18 ES ES493497A patent/ES8105995A1/es not_active Expired
- 1980-07-18 FI FI802283A patent/FI802283A7/fi not_active Application Discontinuation
- 1980-07-21 DK DK313580A patent/DK313580A/da not_active Application Discontinuation
- 1980-07-21 SE SE8005287A patent/SE8005287L/xx unknown
- 1980-07-21 JP JP9974080A patent/JPS5620573A/ja active Pending
- 1980-07-21 LU LU82648A patent/LU82648A1/fr unknown
- 1980-07-23 CA CA356,861A patent/CA1132570A/en not_active Expired

Also Published As

Publication number	Publication date
SE8005287L (sv)	1981-01-27
AR226853A1 (es)	1982-08-31
NO802137L (no)	1981-01-27
ATA363280A (de)	1984-02-15
PT71539A (en)	1980-08-01
LU82648A1 (fr)	1981-02-02
ES493497A0 (es)	1981-07-01
DK313580A (da)	1981-01-27
US4223149A (en)	1980-09-16
ES8105995A1 (es)	1981-07-01
GR69739B (de)	1982-07-09
FI802283A7 (fi)	1981-01-01
ZA804171B (en)	1981-07-29
CA1132570A (en)	1982-09-28
JPS5620573A (en)	1981-02-26

Publication	Publication Date	Title
US4723011A (en)	1988-02-02	Preparation of substituted and disubstituted-pyridine-2,3-dicarboxylate esters
FI66849B (fi)	1984-08-31	Foerfarande foer framstaellning av terapeutiskt anvaendbara 2(h)-pyridinonderivat
Mohamed et al.	2017	Synthesis and anticancer activity of novel 2-substituted pyranopyridine derivatives
Heravi et al.	2013	Recent advances in synthesis of 2-pyridones: a key heterocycle is revisited
NL8004103A (nl)	1981-01-28	Werkwijze ter bereiding van 1.2-dihydro 2-oxo 5-(pyridinyl)nicotinonitrilen.
Potts et al.	1981	Ketenedithioacetals as synthetic intermediates. A versatile synthesis of pyridenes, polypyridinyls, and pyrylium salts
CA1167851A (en)	1984-05-22	Process for preparing 1,2-dihydro-6-methyl-2-oxo-5- (pyridinyl) nicotinonitriles
SU906376A3 (ru)	1982-02-15	Способ получени производных 2-нитроаминопиримидона-4
US4413127A (en)	1983-11-01	Preparation of 1,2-dihydro-6-(lower alkyl)-2-oxo-5-(pyridinyl)nicotinonitriles
Noroozi Pesyan et al.	2020	4‐Methyl morpholinium bis‐(thio) barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study
Orie	2021	Syntheses, complexation and biological activity of aminopyridines: a mini-review
CN119330879B (zh)	2025-09-30	一种喹啉类化合物的合成方法
Takahashi et al.	1992	One-Pot Synthesis and Redox Properties of Conjugation-Extended 4, 4'-Bipyridines and Related Compounds. New Ligands Consisting of a Heterocyclic Three-Ring Assembly.
CA1183139A (en)	1985-02-26	Process for preparing 1,2-dihydro-6-alkyl-2-oxo-5- (pyridinyl) nicotinonitrile or-nicotinamide
US4474953A (en)	1984-10-02	Process and intermediates for the preparation of 3(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones
US4417054A (en)	1983-11-22	2-(Lower-alkoxy)-1-(pyridinyl)ethenyl lower-alkyl ketones
CA1175838A (en)	1984-10-09	N-hydroxy-1,2-dihydro-2-oxo- 5(pyridinyl)nicotinimidamides, their cardiotonic use, their preparation and conversion to corresponding 3- amino-5-(pyridinyl)-2(1h)-pyridinones
Coppola et al.	1980	Pyrimidones. 2. Synthesis and reactions of 2‐chloropyrimidines
Brown et al.	1989	Isocytosine H2-receptor histamine antagonists II. Synthesis and evaluation of biological activity at histamine H1-and H2-receptors of 5-(heterocyclyl) methylisocytosines
KR880001054B1 (ko)	1988-06-18	1, 2-디하이드로-6-메틸-2-옥소-5-(피리디닐)니코티노니트릴의 제조방법
CA1155852A (en)	1983-10-25	6-alkyl-5-(pyridinyl)-3-substituted-2(1h)-pyridinones, useful as cardiotonic agents and their preparation
SE451722B (sv)	1987-10-26	1-pyridinyl-2-(dialkylamino)-etenyl-alkylketoner anvendbara som intermediater vid framstellning av pyridinoner med kardiotoniska egenskaper
Liu et al.	2010	Simple Selective Synthesis of 2, 4-and 2, 6-Diarylpyridines through Metal-Free Cyclocondensation of Aromatic Ketones with Ammonium Acetate
Sammes et al.	1978	The reaction between 4-methoxy-2, 6-dimethylpyrylium perchlorate and amines. Isolation of both 4-iminiopyran salts and pyridinium salts in the reaction with primary amines
Wiley et al.	1961	2, 6-Dimethyl-4-(3'-pyridyl) pyridine-3, 5-dicarboxylic acid and products derived therefrom

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1985-03-01	BV	The patent application has lapsed