☆ 4.8 Article

DMSO as a Dual Carbon Synthon and Water as Oxygen Donor for the Construction of 1,3,5-Oxadiazines from Amidines

ORGANIC LETTERS (2021)

Journal

ORGANIC LETTERS

Volume 23, Issue 10, Pages 3960-3964

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/acs.orglett.1c01116

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Chemistry, Organic

Funding

Leading Innovative and Entrepreneur Team Introduction Program of Zhejiang [2019R01005]

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Abstract

This study established a selective and efficient synthesis of diaryl 1,3,5-oxadiazines for the first time from amidines in wet DMSO. The reaction involved the formation of two new C-N and two new C-O bonds, with DMSO acting as a dual carbon synthon and water providing the oxygen atom for constructing the oxadiazine ring.

A selective and efficient synthesis of diaryl 1,3,5-oxadiazines was established for the first time from simple and readily available amidines in wet DMSO. DMSO was employed as a dual carbon synthon and water offered the oxygen atom to construct the oxadiazine ring. The reaction involved two new C-N and two new C-O bond formations.

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