Abstract

The intermolecular cyclization of N-benzyl-2-cyanoacetamide with carbon disulfide followed by intramolecular cyclization gave thioxothiazinone 3. This compound was used to synthesize a series of novel fused furopyrrole, pyridine, pyrimidine and other azine and azole derivatives. The Michael-type reaction of compound 3 with maleic anhydride followed by pyrrole and furan cyclizations and aromatization yielded polycyclic compound 7. The [3+3]-cycloaddition of benzylidene malononitrile and its derivative to compound 3 gave pyridothiazines 10–12. The ring opening in compound 3 under the action of urea or thiourea followed by pyrimidine cyclization and subsequent air oxidation resulted in the synthesis of oxa- and thiadiazolopyrimidinones 15 and 16, respectively. The reaction of compound 3 with H₂O₂ in a basic medium provided pyrimidine derivative 17. The oxidation of compound 3 with Br₂ in an acid medium led to bromo derivative 19. The synthesized novel compounds were characterized by elemental analysis and IR and ¹H and ¹³C NMR spectroscopy and tested antibacterial and anticancer activities.

中文翻译：

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氰乙酰胺衍生物的杂环化：新型偶氮和叠氮的合成和生物活性。

摘要

N-苄基-2-氰基乙酰胺与二硫化碳的分子间环化，然后进行分子内环化，得到噻吨噻嗪酮3。该化合物用于合成一系列新颖的呋喃并吡咯，吡啶，嘧啶以及其他嗪和唑衍生物。化合物3与马来酸酐的迈克尔型反应，然后进行吡咯和呋喃环化和芳构化，得到多环化合物7。亚苄基丙二腈及其衍生物与化合物3的[3 + 3]-环加成反应得到吡啶并噻嗪10-12。化合物3中的开环在尿素或硫脲的作用下，然后进行嘧啶环化和随后的空气氧化，分别合成了氧杂-和噻二唑并嘧啶酮15和16。在碱性介质中化合物3与H ₂ O ₂的反应提供了嘧啶衍生物17。在酸性介质中用Br ₂氧化化合物3生成溴代衍生物19。合成的新型化合物通过元素分析，IR和¹ H和¹³ C NMR光谱进行表征，并测试了抗菌和抗癌活性。