Microwave-assisted Dimroth Rearrangement of Thiazines to Dihydropyrimidinethiones: Synthetic and Mechanistic Aspects

T.N. Glasnov, D.J. Vugts, M.M. Koningstein, B. Desai, W.M.F. Fabian, R.V.A. Orru, C.O. Kappe

Research output: Contribution to JournalArticleAcademicpeer-review

Abstract

The Dimroth rearrangement of a set of substituted 2-amino-6H-1,3-thiazines into 3,4-dihydropyrimidine-2-thiones was investigated. The rearrangements were carried out under microwave irradiation conditions in batch or continuous flow format, employing either toluene or 1-methyl-2-pyrrolidone as solvent. Thiazines bearing an ester group at the C5 position rearranged at a considerably higher temperature than derivatives without substituents at this position into the corresponding pyrimidinethiones. This strictly thermal rearrangement was studied in detail using differential scanning calorimetry and density functional theory computational methods. The reaction pathway involves a zwitterionic intermediate. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
Original languageEnglish
Pages (from-to)509
JournalQSAR and Combinatorial Science
Volume25
DOIs
Publication statusPublished - 2006

Fingerprint

Dive into the research topics of 'Microwave-assisted Dimroth Rearrangement of Thiazines to Dihydropyrimidinethiones: Synthetic and Mechanistic Aspects'. Together they form a unique fingerprint.

Cite this