Chebanov Valentin A, Muravyova Elena A, Desenko Sergey M, Musatov Vladimir I, Knyazeva Irina V, Shishkina Svetlana V, Shishkin Oleg V, Kappe C Oliver
Department of Chemistry of Heterocyclic Compounds, State Scientific Institution Institute for Single Crystals of National Academy of Sciences of Ukraine, Kharkiv.
J Comb Chem. 2006 May-Jun;8(3):427-34. doi: 10.1021/cc060021a.
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-triazolo[1,5-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-triazolo[1,5-a]pyrimidine-6-carboxamides was established. The described synthetic protocols provide rapid access to novel and diversely substituted dihydroazolopyrimidine libraries.
多组分反应（MCRs）和微波辅助有机合成（MAOS）已被用作合成稠合二氢嘧啶衍生物的关键方法。在微波辐射下，3-氨基-5-烷基硫代-1,2,4-三唑与芳香醛和乙酰乙酰胺的三组分缩合反应被开发为一种快速有效的溶液相方法，用于高产率制备7-芳基-2-烷基硫代-4,7-二氢-1,2,4-三唑并[1,5-a]嘧啶-6-甲酰胺文库。此外，还实现了将生成的二氢三唑并嘧啶选择性还原为反式-反式-2-烷基硫代-7-芳基-4,5,6,7-四氢-1,2,4-三唑并[1,5-a]嘧啶-6-甲酰胺。所描述的合成方案能够快速获得新型且具有多样取代基的二氢唑并嘧啶文库。
