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Synthesis and characterization of some new pyridines, thieno[2,3‐b] pyridines and pyrido[3′,2′:4,5]thieno[3,2‐d]pyrimidine‐4(3H)‐ones bearing styryl moiety
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-03-11 , DOI: 10.1002/jhet.3954 Safiyyah A. H. Al‐Waleedy 1, 2 , Etify A. Bakhite 1 , Mohamed S. Abbady 1 , Hajjaj H. M. Abdu‐Allah 3
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-03-11 , DOI: 10.1002/jhet.3954 Safiyyah A. H. Al‐Waleedy 1, 2 , Etify A. Bakhite 1 , Mohamed S. Abbady 1 , Hajjaj H. M. Abdu‐Allah 3
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3‐Cyano‐5‐ethoxycarbonyl‐6‐methyl‐4‐styrylpyridine‐2(1H )‐thione (3 ) was prepared by reaction of 2‐cyano‐5‐phenylpenta‐2,4‐dienethioamide (2 ) with ethyl acetoacetate or by multicomponent reaction of cinnamaldehyde (1 ), cyanothioacetamide and ethyl acetoacetate in a moderate yield. Reaction of compound 3 with some N ‐aryl‐2‐chloroacetamides, in the presence of sodium acetate, gave the corresponding 2‐(N ‐arylcarbamoylmethylsulfanyl)‐3‐cyano‐5‐ethoxycarbonyl‐6‐methyl‐4‐styrylpyridines 4a‐f . When compounds 4a‐f were subjected to Thorpe‐Ziegler reaction conditions, they converted into the corresponding 3‐amino‐5‐ethoxycarbonyl‐2‐(N ‐arylcarbamoyl)‐6‐methyl‐4‐styrylthieno[2,3‐b ]pyridines 5a‐f . Compounds 5a,e,f were reacted, in turn, with 2,5‐dimethoxytetrahydrofuran to furnish the corresponding 3‐(pyrrol‐1‐yl)thieno‐pyridines 6a,e,f . Reactions of 5a‐f with triethyl orthoformate or nitrous acid were also carried out and their products were identified. Structural formulas of all synthesized compounds was characterized and confirmed on the basis of their elemental and spectral analyses.
中文翻译：
某些带有苯乙烯基的吡啶，噻吩并[2,3-b]吡啶和吡啶并[3'，2'：4,5]噻吩并[3,2-d]嘧啶-4（3H）-的合成和表征
3-氰基-5-乙氧基羰基-6-甲基-4-苯乙烯基吡啶-2-（1 H）-硫酮（3）是通过2氰基-5-苯基戊基-2,4-二烯硫酰胺（2）与乙酰乙酸乙酯反应制得的或通过肉桂醛（1），氰基硫代乙酰胺和乙酰乙酸乙酯的多组分反应以中等收率。化合物3与一些N-芳基-2-氯乙酰胺在乙酸钠存在下反应，得到相应的2-（N-芳基氨基甲酰基甲基硫烷基）-3-氰基-5-乙氧基羰基-6-甲基-4-苯乙烯基吡啶4a-f。当化合物4a-f经受了索普-齐格勒反应条件的影响，它们转化为相应的3-氨基-5-乙氧羰基-2-（N-芳基氨基甲酰基）-6-甲基-4-苯乙烯基噻吩并[2,3- b ]吡啶5a-f。依次将化合物5a，e，f与2,5-二甲氧基四氢呋喃反应，得到相应的3-（吡咯-1-基）噻吩并吡啶6a，e，f。的反应图5a-f的与原甲酸三乙酯或亚硝酸也进行了与他们的产品进行鉴定。根据所有元素的元素分析和光谱分析对所有合成化合物的结构式进行表征和确认。
更新日期：2020-03-11
中文翻译：
某些带有苯乙烯基的吡啶，噻吩并[2,3-b]吡啶和吡啶并[3'，2'：4,5]噻吩并[3,2-d]嘧啶-4（3H）-的合成和表征
3-氰基-5-乙氧基羰基-6-甲基-4-苯乙烯基吡啶-2-（1 H）-硫酮（3）是通过2氰基-5-苯基戊基-2,4-二烯硫酰胺（2）与乙酰乙酸乙酯反应制得的或通过肉桂醛（1），氰基硫代乙酰胺和乙酰乙酸乙酯的多组分反应以中等收率。化合物3与一些N-芳基-2-氯乙酰胺在乙酸钠存在下反应，得到相应的2-（N-芳基氨基甲酰基甲基硫烷基）-3-氰基-5-乙氧基羰基-6-甲基-4-苯乙烯基吡啶4a-f。当化合物4a-f经受了索普-齐格勒反应条件的影响，它们转化为相应的3-氨基-5-乙氧羰基-2-（N-芳基氨基甲酰基）-6-甲基-4-苯乙烯基噻吩并[2,3- b ]吡啶5a-f。依次将化合物5a，e，f与2,5-二甲氧基四氢呋喃反应，得到相应的3-（吡咯-1-基）噻吩并吡啶6a，e，f。的反应图5a-f的与原甲酸三乙酯或亚硝酸也进行了与他们的产品进行鉴定。根据所有元素的元素分析和光谱分析对所有合成化合物的结构式进行表征和确认。
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