2019Russian Journal of Organic ChemistryRequires access

Synthesis and Azido-Tetrazole Tautomerism of New Methylsulfanyl Thieno[3,2-d]pyrimidine Derivatives

Samvel N. Sirakanyan, Elmira K. Hakobyan, Anush A. Hovakimyan

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Abstract

New 7-amino, 7-azido, and 7-alkylsulfanyl derivatives have been synthesized from 7-chloro-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1 H -cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2- d ]pyrimidine. 7-Azido-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1 H -cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2- d ]-pyrimidine has been found to exist in solution as a mixture of azido and tetrazole tautomers, whereas only its tetrazole form is present in the crystalline state.

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What this paper is about

New 7-amino, 7-azido, and 7-alkylsulfanyl derivatives have been synthesized from 7-chloro-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1 H -cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2- d ]pyrimidine. 7-Azido-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1 H -cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2- d ]-pyrimidine has been found to exist in solution as a mixture of azido and tetrazole tautomers, whereas only its tetrazole form is present in the crystalline state.

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Available abstract

New 7-amino, 7-azido, and 7-alkylsulfanyl derivatives have been synthesized from 7-chloro-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1 H -cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2- d ]pyrimidine. 7-Azido-9-(methylsulfanyl)-4-(propan-2-yl)-2,3-dihydro-1 H -cyclopenta[4′,5′]pyrido[3′,2′:4,5]thieno[3,2- d ]-pyrimidine has been found to exist in solution as a mixture of azido and tetrazole tautomers, whereas only its tetrazole form is present in the crystalline state.

Key concepts: Tautomer, Tetrazole, Chemistry, Pyrimidine, Stereochemistry, Medicinal chemistry

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Synthesis and Azido-Tetrazole Tautomerism of New Methylsulfanyl Thieno[3,2-d]pyrimidine Derivatives — Research Paper | ScholarLens