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Updated: Jan 11, 2026

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Cascade [5 + 1] Cycloaddition of 1-Diazonaphthalen-2(1H)-ones with Sulfoxonium Ylides for the Synthesis of
Jin-Mei Qi1, Qin Luo1, Ke-Hua Zhao1
1Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
Abstract:
We developed a novel protocol for the synthesis of functionalized 1H-naphtho[1,2-e][1,3,4]oxadiazines (NODZs) 3 from 1-diazonaphthalen-2(1H)-ones with sulfoxonium ylides via a [5 + 1] cycloaddition. This process involves heating a mixture of substrates with DCM catalyzed by Sc(OTf)3, resulting in the cleavage of a C═S bond and the formation of C-O and C═N bonds. The reaction consists of a [3 + 2] cycloaddition followed by intramolecular cyclization, coupled with the elimination of DMSO and an H atom through [1,3] σ-migration. Significantly, 1-diazonaphthalen-2(1H)-one acts as a C5 synthon, enabling capture by sulfoxonium ylides. This work demonstrates the utility of 1-diazonaphthalen-2(1H)-one as a C5 synthon and paves the way for synthesizing diverse cyclic structures via different cycloaddition strategies. These methodologies may also facilitate the one-pot synthesis of functionalized N-oxadiazolines and their derivatives for combinatorial applications.
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