Microwave-assisted three-component synthesis of 7-aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo[1,5-a]-pyrimidine-6-carboxamides and their selective reduction |
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Authors: | Chebanov Valentin A Muravyova Elena A Desenko Sergey M Musatov Vladimir I Knyazeva Irina V Shishkina Svetlana V Shishkin Oleg V Kappe C Oliver |
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Institution: | Department of Chemistry of Heterocyclic Compounds, State Scientific Institution Institute for Single Crystals of National Academy of Sciences of Ukraine, Kharkiv. chebanov@isc.kharkov.com |
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Abstract: | Multicomponent reactions (MCRs) and microwave-assisted organic synthesis (MAOS) have been used as key methods for the synthesis of fused dihydropyrimidine derivatives. The three-component condensation of 3-amino-5-alkylthio-1,2,4-triazoles with aromatic aldehydes and acetoacetamides under microwave irradiation was developed as a rapid and efficient solution-phase method for the high-yielding preparation of 7-aryl-2-alkylthio-4,7-dihydro-1,2,4-triazolo1,5-a]pyrimidine-6-carboxamide libraries. In addition, the selective reduction of the formed dihydrotriazolopyrimidines to trans-trans-2-alkylthio-7-aryl-4,5,6,7-tetrahydro-1,2,4-triazolo1,5-a]pyrimidine-6-carboxamides was established. The described synthetic protocols provide rapid access to novel and diversely substituted dihydroazolopyrimidine libraries. |
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