One-Step Assembly of Functionalized Morpholinones and 1,4-Oxazepane-3-ones via [3 + 3]- And [3 + 4]-Annulation of Aza-Oxyallyl Cation and Amphoteric Compounds

Tishyasoumya Bera, Bandana Singh, Trevor A. Hamlin, Subash C. Sahoo, Jaideep Saha*

*Corresponding author for this work

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

A new [3 + 3]- and [3 + 4]-annulation strategy involving azaoxyallyl cation and [1,m]-amphoteric compounds (m = 3,4) is presented. This concise method enables easy assembly of functionalized saturated N-heterocycles, comprised of six-and seven-membered rings and is of high significance in the context of drug discovery approaches. This reaction also represents a new trapping modality of the azaoxyallyl cation with amphoteric agents of different chain lengths that consist of a heteroatom nucleophilic site and a π-electrophilic site.

Original languageEnglish
Pages (from-to)15255-15266
Number of pages12
JournalJournal of Organic Chemistry
Volume84
Issue number23
Early online date8 Nov 2019
DOIs
Publication statusPublished - 6 Dec 2019

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