Tetrahedron

Synthesis of asymmetric 3, 5-diaryl-4H-1, 2, 6-thiadiazin-4-ones via Suzuki–Miyaura and Stille coupling reactions

HA Ioannidou, PA Koutentis

Index: Ioannidou, Heraklidia A.; Koutentis, Panayiotis A. Tetrahedron, 2012 , vol. 68, # 36 p. 7380 - 7385

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Citation Number: 5

Abstract

Asymmetric 3, 5-diaryl substituted 4H-1, 2, 6-thiadiazin-4-ones can be prepared from 3, 5- dichloro-4H-1, 2, 6-thiadiazin-4-one (1) via a multi-step protocol: selective nucleophilic mono-chloro substitution gives either the mono-methoxy or benzyloxy substituted mono- chlorothiadiazinones that can be phenylated via Suzuki–Miyaura coupling. Subsequent BBr3 mediated dealkylation gives 3-hydroxy-5-phenyl-4H-1, 2, 6-thiadiazin-4-one (9) that ...