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Paper | Regular issue | Vol 100, No. 6, 2020, pp.881-900
Published online, 28th April, 2020
DOI: 10.3987/COM-20-14244
Convenient Synthesis of 2,3-Dihydro-1,2,4-thiadiazoles, 4,5-Dihydro-1,3-thiazoles, and 1,3-Thiazoles through a [4+1]-Type Oxidative Ring Closure of 1,3-Thiaza-1,3-butadienes

Kazuaki Shimada,* Megumi Isogami, Kitami Maeda, Rei Nishinomiya, and Toshinobu Korenaga

*Department of Chemistry and Biosciences, Faculty of Science and Engineering, Iwate University, Morioka, Iwate 020-8551, Japan

Abstract

1,3-Thiaza-1,3-butadienes bearing an N,N-dimethylamino group at the C-2 position were efficiently converted into 5H-1,2,4-oxathiazoles, 2,3-dihydro-1,2,4-thiadiazoles, 4,5-dihydro-1,3-thiazoles, and 1,3-thiazoles through an oxidative ring closure by treating with mCPBA, chloramine-T, metal carbenoids, or dichlorocarbene, respectively, via the ring closure of in situ generated heterocumulene-type reactive species involving thione S-oxides, thione S-imides, and thiocarbonyl ylides.