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Synthesis of Pentasubstituted Pyridines. IV—Structural Characterization of the Addition Products of 1–( N,N –Diethylamine)prop–1–yne to N –Vinylcarbodiimides and –ketenimines
Author(s) -
PeláezArango Elvira,
Ferrero Miguel,
LópezOrtiz Fernando
Publication year - 1996
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199605)34:5<368::aid-omr890>3.0.co;2-0
Subject(s) - chemistry , diethylamine , pyridine , cycloaddition , medicinal chemistry , ton , stereochemistry , electrocyclic reaction , proton nmr , ring (chemistry) , computational chemistry , organic chemistry , catalysis , fishery , biology
The reaction products of the addition of 1‐( N , N ‐diethylamine)prop‐1‐yne to N ‐vinylcarbodiimides and ‐ketenimines have been identified. Two pyridine regioisomers can be obtained under thermal control according to a [4+2] or [2+2] 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.