摘要/Abstract

微波辐射条件下，以乙醇作溶剂，环戊酮、丙二腈与单质硫反应得到2-氨基-5，6-二氢-4H-环戊二烯[b]噻吩-3-腈（1），1与N，N-二甲基甲酰胺二甲基缩醛在微波辐射条件下反应得到N-（3-氰基-5，6-二氢-4H-环戊二烯[b]-硫基-2-基）-N，N-二甲基亚甲基酰胺（2），进一步在微波辐射条件下由N-（3-氰基-5，6-二氢-4H-环戊二烯[b]-硫基-2-基）-N，N-二甲基亚甲基酰胺（2）与取代芳香胺反应制得目标化合物.合成的25个目标化合物通过熔点测定和核磁共振氢谱分析、红外光谱、高分辨质谱对其结构进行确证.
关键词: 6,7-二氢-5H-环戊二烯并[4,5]噻吩并[2,3-d]嘧啶-4-胺, Gewald反应, Dimroth重排, 微波合成
25 kinds of 6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amines were synthesized. Under microwave irradiation conditions, cyclopentanone, malononitrile and elemental sulfur reacted in ethanol to form 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (1). Compound 1 reacted with N,N-dimethylformamide dimethyl acetal to give N-(3-cyano-5,6-dihydro-4H-cyclopenta[b]-thien-2-yl)-N,N-dimethylmethanimidamide (2) under microwave irradiation conditions. Treatment of the compound 2 with aromatic amine under microwave irradiation yielded the corresponding compounds 6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine with good yields. The structures of the 25 target compounds were confirmed by melting point, NMR, IR and HRMS techniques.
Key words: 6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine, Gewald reaction, Dimroth rearrangement, microwave synthesis


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