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Aza‐[4+3] and Aza‐[3+2] Annulations for Synthesis of Dihydroazepines and Dihydropyrroles from Alkynes, Sulfonyl Azides, and 1,3‐Dienes
Author(s) -
Kim Sanghyuck,
Mo Juntae,
Kim Jaeeun,
Ryu Taekyu,
Lee Phil Ho
Publication year - 2014
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201402071
Subject(s) - annulation , chemistry , combinatorial chemistry , sulfonyl , two step , stereochemistry , organic chemistry , catalysis , alkyl
Abstract We report aza‐[4+3] annulation through sequential [3+2]‐[2+1] cycloadditions‐aza‐Cope rearrangement for the synthesis of dihydroazepines. Aza‐[3+2] annulation was achieved through [3+2]‐[2+1]‐aza‐Cope rearrangement‐1,3‐migration or [3+2]‐[2+1]‐Clock rearrangement, leading to the formation of dihydropyrroles. In addition, dihydroazepines thermally 1,3‐migrated to give dihydropyrroles. This method affords a straightforward synthetic pathway from simple triazoles to produce dihydroazepines and dihydropyrroles together with N 2 as the single byproduct. This procedure can be successfully applied to a one‐pot process starting from terminal alkynes, azides, and dienes.