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

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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

Funding

J.S. thanks SERB, New Delhi (ECR/2016/001474) for funding. T.S.B is an INSPIRE-JRF and B.S. thank CSIR, New Delhi for fellowship. J.S. thanks Director CBMR for research facilities. J.S. sincerely thanks Prof. Andrei Yudin (U Toronto) for some important comments on this work. S.S thanks DST-FIST for the single crystal X-ray facility at Punjab University (P.U), Chandigarh.

FundersFunder number
INSPIRE-JRF
Council of Scientific and Industrial Research, India
Science and Engineering Research BoardECR/2016/001474

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