Cyclization of 2-dicyanomethylene-1,2-dihydro-pyridine-3-carbonitriles with hydrogen halides: A re-examination on the regioselectivity

Pedro Victory; Núria Busquets; JoséI I. Borrell; Jordi Teixidó; Blanca Serra; Josep Lluís Matallana; Hans Junek; Heinz Sterk

doi:10.3987/com-95-7037

Cyclization of 2-dicyanomethylene-1,2-dihydro-pyridine-3-carbonitriles with hydrogen halides: A re-examination on the regioselectivity

Pedro Victory, Núria Busquets, JoséI I. Borrell, Jordi Teixidó, Blanca Serra, Josep Lluís Matallana, Hans Junek, Heinz Sterk

Department of Organic and Pharmaceutical Chemistry

Research output: Indexed journal article › Article › peer-review

17 Citations (Scopus)

Abstract

The cyclization of the title compounds (5a-c) with HCl and HBr has been re-examined. In all cases 5-amino-7-halo-substituted 1,6-naphthyridines (11a-c and 12a-c) were formed independently of the thermal level and the hydrogen halide employed. The structures of 11a-c and 12a-c were unequivocally established by reaction with hydrazine which afforded the corresponding pyrazolo[3,4-h][1,6]naphthyridines (14a-c). The structure of the methoxy derivatives (15a,c and 16a,c) was assigned by two-dimensional nmr studies.

Original language	English
Pages (from-to)	1013-1022
Number of pages	10
Journal	Heterocycles
Volume	41
Issue number	5
DOIs	https://doi.org/10.3987/com-95-7037
Publication status	Published - 1 May 1995

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title = "Cyclization of 2-dicyanomethylene-1,2-dihydro-pyridine-3-carbonitriles with hydrogen halides: A re-examination on the regioselectivity",

abstract = "The cyclization of the title compounds (5a-c) with HCl and HBr has been re-examined. In all cases 5-amino-7-halo-substituted 1,6-naphthyridines (11a-c and 12a-c) were formed independently of the thermal level and the hydrogen halide employed. The structures of 11a-c and 12a-c were unequivocally established by reaction with hydrazine which afforded the corresponding pyrazolo[3,4-h][1,6]naphthyridines (14a-c). The structure of the methoxy derivatives (15a,c and 16a,c) was assigned by two-dimensional nmr studies.",

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T1 - Cyclization of 2-dicyanomethylene-1,2-dihydro-pyridine-3-carbonitriles with hydrogen halides

T2 - A re-examination on the regioselectivity

AU - Victory, Pedro

AU - Busquets, Núria

AU - Borrell, JoséI I.

AU - Teixidó, Jordi

AU - Serra, Blanca

AU - Matallana, Josep Lluís

AU - Junek, Hans

AU - Sterk, Heinz

PY - 1995/5/1

Y1 - 1995/5/1

N2 - The cyclization of the title compounds (5a-c) with HCl and HBr has been re-examined. In all cases 5-amino-7-halo-substituted 1,6-naphthyridines (11a-c and 12a-c) were formed independently of the thermal level and the hydrogen halide employed. The structures of 11a-c and 12a-c were unequivocally established by reaction with hydrazine which afforded the corresponding pyrazolo[3,4-h][1,6]naphthyridines (14a-c). The structure of the methoxy derivatives (15a,c and 16a,c) was assigned by two-dimensional nmr studies.

AB - The cyclization of the title compounds (5a-c) with HCl and HBr has been re-examined. In all cases 5-amino-7-halo-substituted 1,6-naphthyridines (11a-c and 12a-c) were formed independently of the thermal level and the hydrogen halide employed. The structures of 11a-c and 12a-c were unequivocally established by reaction with hydrazine which afforded the corresponding pyrazolo[3,4-h][1,6]naphthyridines (14a-c). The structure of the methoxy derivatives (15a,c and 16a,c) was assigned by two-dimensional nmr studies.

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Cyclization of 2-dicyanomethylene-1,2-dihydro-pyridine-3-carbonitriles with hydrogen halides: A re-examination on the regioselectivity

Abstract

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