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

^*Corresponding author for this work

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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.

Original language	English
Pages (from-to)	1-6
Number of pages	6
Journal	Heterocycles
Volume	36
Issue number	1
DOIs	https://doi.org/10.3987/com-92-6138
Publication status	Published - 1 Jan 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",

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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

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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.

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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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