We describe a simple method to synthesize novel 4-cyano-1-morpholin-4-yl-6,7-dihydro-5H-cyclopenta[c]pyridine-3-thione by the reaction of 3-amino-1-thioxo-1,5,6,7-tetrahydrocyclopenta[c]thiopyran-4-carbonitrile with morpholine through Dimroth rearrangement. The 1-amino-5-morpholin-4-yl-7,8-dihydro-6H-cyclopenta[d]thieno[2,3-b]pyridine-2-carboxamide, which was synthesized by two methods, was used as a versatile precursor for synthesis of new thienopyrimidines fused to cyclopenta[d]pyridine ring system. Consequently, reaction of the amino-carboxamide with diethylmalonate, triethyl orthoformate, and cycloalkanones afforded the corresponding fused pyrimidine heterocycles. On the other hand, chloroacetylation of the amino-carboxamide using chloroacetyl chloride in dioxane produced the chloroacetyl amino derivative that in turn underwent cyclocondensation upon reaction with acetic anhydride to give the chloromethyl pyrimidinone. The latter compound was subjected to react with various nitrogen nucleophiles by nucleophilic substitution reactions to yield the akyl (aryl)amino methyl pyrimidinones. Subsequently, treatment of the phenyl aminomethyl derivative with formaldehyde under Mannich conditions produced the imidazopyridothienopyrimidine ring system. Similarly, reaction of the phenyl aminomethyl pyrimidonone with chloroacetyl chloride afforded a new heterocyclic system namely, cyclopentapyridothienopyrimidopyrazine. On the other hand, reaction of the amino-carboxamide with carbon disulfide in pyridine led to the formation of oxopyrimidine thione, which was alkylated by the reaction with different α-halo carbonyl compounds. The newly synthesized compounds were fully characterized on the basis of elemental and spectral analyses. Alternatively, some of these compounds revealed promising antibacterial and antifungal activities through the in vitro screening.

中文翻译：

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含有环戊二烯[d]噻吩并[2,3-b]吡啶部分和相关稠杂环的新型杂环化合物的合成、反应和抗菌活性

我们描述了一种通过 3-amino-1-thioxo-1 反应合成新型 4-cyano-1-morpholin-4-yl-6,7-dihydro-5H-cyclopenta[c]pyridine-3-thone 的简单方法,5,6,7-四氢环戊二烯[c]thiopyran-4-carbonitrile 与吗啉通过 Dimroth 重排。通过两种方法合成的 1-amino-5-morpholin-4-yl-7,8-dihydro-6H-cyclopenta[d]thieno[2,3-b]pyridine-2-carboxamide 作为用于合成与环戊二烯[d]吡啶环系统稠合的新型噻吩并嘧啶的通用前体。因此，氨基甲酰胺与丙二酸二乙酯、原甲酸三乙酯和环烷酮反应得到相应的稠合嘧啶杂环。另一方面，在二恶烷中使用氯乙酰氯对氨基甲酰胺进行氯乙酰化，产生氯乙酰氨基衍生物，该衍生物在与乙酸酐反应后发生环缩合反应，得到氯甲基嘧啶酮。后一种化合物通过亲核取代反应与各种含氮亲核试剂反应，得到烷基（芳基）氨基甲基嘧啶酮。随后，在曼尼希条件下用甲醛处理苯基氨基甲基衍生物产生咪唑并吡啶并噻吩并嘧啶环系统。类似地，苯基氨基甲基嘧啶酮与氯乙酰氯的反应提供了一个新的杂环系统，即环戊吡啶并噻吩并嘧啶吡嗪。另一方面，氨基甲酰胺与二硫化碳在吡啶中的反应导致形成氧代嘧啶硫酮，硫酮通过与不同的 α-卤代羰基化合物反应而被烷基化。新合成的化合物在元素和光谱分析的基础上得到了充分表征。或者，其中一些化合物通过体外筛选显示出有希望的抗菌和抗真菌活性。