Aza‐[4+3] and Aza‐[3+2] Annulations for Synthesis of Dihydroazepines and Dihydropyrroles from Alkynes, Sulfonyl Azides, and 1, 3‐Dienes. Issue 9 (16th June 2014)

• Record Type: Journal Article
• Authors: Kim, Sanghyuck; Mo, Juntae; Kim, Jaeeun; Ryu, Taekyu; Lee, Phil Ho
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 9(2014:Sep.)
• Page Start: 926
• Page End: 931
• Publication Date: 2014-06-16
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201402071
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 N₂ as the single byproduct. This procedure can be successfully applied to a one‐pot process starting from terminal alkynes, azides, and dienes.</p> </abstract>