Synthesis of Pyrimidine-Annulated Heterocycles: Facile Sulfoxide Rearrangement of 1, 3-Dimethyl-5-(Aryloxybut-2-Ynylthio) Pyrimidine-2, 4-Dione (SUPPORTING DATA)

Krishna   C.   Majumdar; Pradip   K.   Maji; Amarta   K.   Pal

doi:10.2174/157017807780414127

Abstract

A number of thieno [3,2-b] pyrimidines are regioselectively synthesized in good yields from 5-(4- aryloxybut-2-ynylthio) via sulfoxide rearrangement/tandem cyclization protocol by the treatment of the sulfides with one equivalent of m-CPBA in chloroform at 0-5°C with stirring the reaction mixture at room temperature for 2 h.

Keywords: 5-Mercaptouracil, tandem reaction, [2,3] sigmatropic rearrangement, [3,3] sigmatropic rearrangement, thienopyrimidine

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Letters in Organic Chemistry

Title: Synthesis of Pyrimidine-Annulated Heterocycles: Facile Sulfoxide Rearrangement of 1, 3-Dimethyl-5-(Aryloxybut-2-Ynylthio) Pyrimidine-2, 4-Dione (SUPPORTING DATA)

Volume: 4 Issue: 2

Author(s): Krishna C. Majumdar, Pradip K. Maji and Amarta K. Pal

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Keywords: 5-Mercaptouracil, tandem reaction, [2,3] sigmatropic rearrangement, [3,3] sigmatropic rearrangement, thienopyrimidine

Abstract: A number of thieno [3,2-b] pyrimidines are regioselectively synthesized in good yields from 5-(4- aryloxybut-2-ynylthio) via sulfoxide rearrangement/tandem cyclization protocol by the treatment of the sulfides with one equivalent of m-CPBA in chloroform at 0-5°C with stirring the reaction mixture at room temperature for 2 h.

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Majumdar C. Krishna, Maji K. Pradip and Pal K. Amarta, Synthesis of Pyrimidine-Annulated Heterocycles: Facile Sulfoxide Rearrangement of 1, 3-Dimethyl-5-(Aryloxybut-2-Ynylthio) Pyrimidine-2, 4-Dione (SUPPORTING DATA), Letters in Organic Chemistry 2007; 4 (2) . https://dx.doi.org/10.2174/157017807780414127