The Dimroth Rearrangement: Synthesis and Interconversion of Isomeric Triazolothienopyrimidines

Author:

Hamed Atef A.1,El-Ashry El-Sayed H.2,Zeid Ibrahim F.1,Badr Hesham F.1

Affiliation:

1. Chemistry Department, Faculty of Science, Menoufia University, Egypt

2. Chemistry Department, Faculty of Science, Alexandria University, Egypt

Abstract

Triazolo-thieno[3,2- e]pyrimidines obtained by cyclisation of 4-hydrazino-2-(methylthio)thieno[2,3- d]pyrimidine with formic acid, acetic acid, cyanogen bromide and carbon disulfide, and by oxidation of the derived aldehyde hydrazones, are found to be the triazolo[4,3- c] isomers. These [4,3- c] compounds resist isomerisation in acid, but they undergo Dimroth rearrangement to the [1,5- c] isomers under basic conditions. The crystal structure of one such rearranged product, 5-methoxy-8,9,10,11-tetrahydro[1]benzothieno[3,2- e][1,2,4]triazolo[1,5- c]pyrimidine (13b) was confirmed by X-ray analysis.

Publisher

SAGE Publications

Subject

General Chemistry

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