1,2,3,4-Tetrahydro-1,6-naphthyridines. Part 2. Formation and unexpected reactions of 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2, 7-diones

Pedro J. Victory; Jordi Teixidó; JoséI I. Borrell; Núria Busquets

doi:10.3987/com-92-6138

1,2,3,4-Tetrahydro-1,6-naphthyridines. Part 2. Formation and unexpected reactions of 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2, 7-diones

Pedro J. Victory, Jordi Teixidó, JoséI I. Borrell, Núria Busquets

Departament de Química Orgànica i Farmacèutica

Producció científica: Article en revista indexada › Article › Avaluat per experts

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The nucleophilic substitution of the enol methoxy group of pyridones (1) by methyl cyanoacetate led to (Z)-5-cyano-6-cyanomethoxycarbonylmethylenepiperidones (6), which underwent cyclization in acid medium to 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2,7-diones (7). Surprisingly, the treatment of 7 with ammonia yielded the 5-cyano-6-cyanomethyl substituted pyridones (11) which were not accessible by reaction of 1 with NaCH₂CN.

Idioma original	Anglès
Pàgines (de-a)	1-6
Nombre de pàgines	6
Revista	Heterocycles
Volum	36
Número	1
DOIs	https://doi.org/10.3987/com-92-6138
Estat de la publicació	Publicada - 1 de gen. 1993

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title = "1,2,3,4-Tetrahydro-1,6-naphthyridines. Part 2. Formation and unexpected reactions of 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2, 7-diones",

abstract = "The nucleophilic substitution of the enol methoxy group of pyridones (1) by methyl cyanoacetate led to (Z)-5-cyano-6-cyanomethoxycarbonylmethylenepiperidones (6), which underwent cyclization in acid medium to 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2,7-diones (7). Surprisingly, the treatment of 7 with ammonia yielded the 5-cyano-6-cyanomethyl substituted pyridones (11) which were not accessible by reaction of 1 with NaCH2CN.",

author = "Victory, {Pedro J.} and Jordi Teixid{\'o} and Borrell, {Jos{\'e}I I.} and N{\'u}ria Busquets",

year = "1993",

month = jan,

day = "1",

doi = "10.3987/com-92-6138",

language = "English",

volume = "36",

pages = "1--6",

journal = "Heterocycles",

issn = "0385-5414",

publisher = "Japan Institute of Heterocyclic Chemistry",

number = "1",

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TY - JOUR

T1 - 1,2,3,4-Tetrahydro-1,6-naphthyridines. Part 2. Formation and unexpected reactions of 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2, 7-diones

AU - Victory, Pedro J.

AU - Teixidó, Jordi

AU - Borrell, JoséI I.

AU - Busquets, Núria

PY - 1993/1/1

Y1 - 1993/1/1

N2 - The nucleophilic substitution of the enol methoxy group of pyridones (1) by methyl cyanoacetate led to (Z)-5-cyano-6-cyanomethoxycarbonylmethylenepiperidones (6), which underwent cyclization in acid medium to 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2,7-diones (7). Surprisingly, the treatment of 7 with ammonia yielded the 5-cyano-6-cyanomethyl substituted pyridones (11) which were not accessible by reaction of 1 with NaCH2CN.

AB - The nucleophilic substitution of the enol methoxy group of pyridones (1) by methyl cyanoacetate led to (Z)-5-cyano-6-cyanomethoxycarbonylmethylenepiperidones (6), which underwent cyclization in acid medium to 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2,7-diones (7). Surprisingly, the treatment of 7 with ammonia yielded the 5-cyano-6-cyanomethyl substituted pyridones (11) which were not accessible by reaction of 1 with NaCH2CN.

UR - http://www.scopus.com/inward/record.url?scp=0004477976&partnerID=8YFLogxK

U2 - 10.3987/com-92-6138

DO - 10.3987/com-92-6138

M3 - Article

AN - SCOPUS:0004477976

SN - 0385-5414

VL - 36

SP - 1

EP - 6

JO - Heterocycles

JF - Heterocycles

IS - 1

ER -

1,2,3,4-Tetrahydro-1,6-naphthyridines. Part 2. Formation and unexpected reactions of 1,2,3,4-tetrahydro-7H-pyrano[4,3-b]pyridine-2, 7-diones

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