Cyclization of 1,5-dinitrile systems with hydrogen halides: A search for the undetected key tautomer

Jordi Teixidó; José I. Borrell; Blanca Serra; Carles Colominas; Xavier Batllori; Joan F. Piniella; Angel Alvarez-Larena

doi:https://doi.org/10.1016/S0040-4020(97)00121-X

Cyclization of 1,5-dinitrile systems with hydrogen halides: A search for the undetected key tautomer

Jordi Teixidó, José I. Borrell, Blanca Serra, Carles Colominas, Xavier Batllori, Joan F. Piniella, Angel Alvarez-Larena

Department of Geology

Research output: Contribution to journal › Article › Research › peer-review

5 Citations (Scopus)

Abstract

The 13C NMR spectra of the pyridones 7a-d recorded in DMSO-d6 show three groups of signals which correspond to the two diastereomers of the 7-exo tautomer and the 7-endo tautomer. The X-ray powder analysis and the molecular structures of 7a-c clearly prove that these compounds, and probably 7d, are present in the solid state as a single diastereomer of the 7-exo tautomer which, on being dissolved, establishes an equilibrium with the other diastereomer through the 7-endo tautomer. This later had been proposed as a hey intermediate in the cyclization of the 1,5-dinitrile system present in 7a-d but was not previously detected.

Original language	English
Pages (from-to)	4487-4496
Journal	Tetrahedron
Volume	53
DOIs	https://doi.org/10.1016/S0040-4020(97)00121-X
Publication status	Published - 24 Mar 1997

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title = "Cyclization of 1,5-dinitrile systems with hydrogen halides: A search for the undetected key tautomer",

abstract = "The 13C NMR spectra of the pyridones 7a-d recorded in DMSO-d6 show three groups of signals which correspond to the two diastereomers of the 7-exo tautomer and the 7-endo tautomer. The X-ray powder analysis and the molecular structures of 7a-c clearly prove that these compounds, and probably 7d, are present in the solid state as a single diastereomer of the 7-exo tautomer which, on being dissolved, establishes an equilibrium with the other diastereomer through the 7-endo tautomer. This later had been proposed as a hey intermediate in the cyclization of the 1,5-dinitrile system present in 7a-d but was not previously detected.",

author = "Jordi Teixid{\'o} and Borrell, {Jos{\'e} I.} and Blanca Serra and Carles Colominas and Xavier Batllori and Piniella, {Joan F.} and Angel Alvarez-Larena",

year = "1997",

month = mar,

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doi = "https://doi.org/10.1016/S0040-4020(97)00121-X",

language = "English",

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pages = "4487--4496",

journal = "Tetrahedron",

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TY - JOUR

T1 - Cyclization of 1,5-dinitrile systems with hydrogen halides: A search for the undetected key tautomer

AU - Teixidó, Jordi

AU - Borrell, José I.

AU - Serra, Blanca

AU - Colominas, Carles

AU - Batllori, Xavier

AU - Piniella, Joan F.

AU - Alvarez-Larena, Angel

PY - 1997/3/24

Y1 - 1997/3/24

N2 - The 13C NMR spectra of the pyridones 7a-d recorded in DMSO-d6 show three groups of signals which correspond to the two diastereomers of the 7-exo tautomer and the 7-endo tautomer. The X-ray powder analysis and the molecular structures of 7a-c clearly prove that these compounds, and probably 7d, are present in the solid state as a single diastereomer of the 7-exo tautomer which, on being dissolved, establishes an equilibrium with the other diastereomer through the 7-endo tautomer. This later had been proposed as a hey intermediate in the cyclization of the 1,5-dinitrile system present in 7a-d but was not previously detected.

AB - The 13C NMR spectra of the pyridones 7a-d recorded in DMSO-d6 show three groups of signals which correspond to the two diastereomers of the 7-exo tautomer and the 7-endo tautomer. The X-ray powder analysis and the molecular structures of 7a-c clearly prove that these compounds, and probably 7d, are present in the solid state as a single diastereomer of the 7-exo tautomer which, on being dissolved, establishes an equilibrium with the other diastereomer through the 7-endo tautomer. This later had been proposed as a hey intermediate in the cyclization of the 1,5-dinitrile system present in 7a-d but was not previously detected.

U2 - https://doi.org/10.1016/S0040-4020(97)00121-X

DO - https://doi.org/10.1016/S0040-4020(97)00121-X

M3 - Article

VL - 53

SP - 4487

EP - 4496

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

ER -