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

✍ Scribed by Elvira Peláez-Arango; Miguel Ferrero; Fernando López-Ortiz

Publisher
John Wiley and Sons
Year
1996
Tongue
English
Weight
414 KB
Volume
34
Category
Article
ISSN
0749-1581

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✦ Synopsis

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 electrocyclic ring closure of the heterocumulene is observed. The structures of the pyridines isolated are assigned by a combination of HMBC and NOE difference spectra.

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