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Synthesis of pentasubstituted pyridines. II—NMR study of the addition products of 1-(N,N-diethylamine)prop-1-yne to methyl 2-isothiocyanato-3-phenylpropenoate

✍ Scribed by Elvira Peláez-Arango; Fernando López-Ortiz; José Barluenga; Miguel Ferrero; Francisco Palacios

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 482 KB
Volume: 32
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1260321103

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✦ Synopsis

Abstract

The structure of the pentasubstituted pyridines obtained in the reaction of methyl 2‐isothiocyanato‐3‐phenylpropenoate with 1‐(N,N‐diethylamine)prop‐1‐yne were assigned based on 2D heteronuclear correlation experiments and NOE measurements. At 0°C a 2‐azabicyclo[2.2.2] octa‐2,7‐diene intermediate was isolated and spectroscopically characterized.

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Synthesis of Pentasubstituted Pyridines.

Synthesis of Pentasubstituted Pyridines. IV—Structural Characterization of the Addition Products of 1–(N,N–Diethylamine)prop–1–yne toN–Vinylcarbodiimides and –ketenimines

✍ Elvira Peláez-Arango; Miguel Ferrero; Fernando López-Ortiz 📂 Article 📅 1996 🏛 John Wiley and Sons 🌐 English ⚖ 414 KB 👁 2 views

The reaction products of the addition of 1-(N,N-diethy1amine)prop-1-yne to N-vinylcarbodiimides and -ketenimines have been identified. Two pyridine regioisomers can be obtained under thermal control according to a 14 + 21 or 12 + 21 cycloaddition mechanism. At temperatures above 100°C a competing el