| 1002554-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1002554-94-0
• 化学式: C₁₆H₁₇ClN₄S
• 分子量: 332.857
• InChiKey: LWFRKZZBXCOSHM-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 以 苯 为溶剂， 反应 0.5h， 以95%的产率得到(4-chlorophenylazo)-(2-methyl-1,3-dioxo-octahydropyrrolo[3,4-a]pyrrolizin-4-ylidene)acetonitrile
  参考文献：
  名称：

  3-Alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)-acrylonitriles as masked 1,3-dipoles

  摘要：

  Reaction of 3-alkylsulfanyl-2-arylazo-3-(pyrrolidin-1-yl)acrylonitriles with maleimides, dimethyl maleate and dimethylacetylene dicarboxylate were carried out to give octahydro-pyrrolo[3,4-alpha]pyrrolizin-4-ylidenes, hexahydro-pyrrolizines and 6,7-dihydro-5H-pyrrolizines. The formation of the synthesized compounds is explained by a 1,3-dipolar cycloaddition of an in situ generated azomethine ylide. The mechanisms of the formation of these active intermediates were discussed with the aid of density functional theory methods with the B3LYP functional 6-31G(+) calculations using the STAN method and chemical experiments. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.114

文献信息

• Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide
  作者：N. P. Belskaya、A. V. Koksharov、T. G. Deryabina、O. S. Eltsov、P. A. Slepukhin、V. A. Bakulev

  DOI：10.1007/s11172-010-0169-1

  日期：2010.4

  Reactions of 2-arylazo-3-(1-azacycloalk-1-yl)-3-methylsulfanylacrylonitriles with male-imide in benzene gave octahydropyrrolo[3,4-a]pyrrolizines 2a–c, decahydro-2,7a-diaza-cyclopenta[a]indene 2e, and decahydro-5-oxa-2,7a-diazacyclopenta[a]indene 2f as a result of 1,3-dipolar cycloaddition. In a similar reaction with 3-allylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles 3, dipolar cycloaddition and intramolecular cyclization competed to give a mixture of compounds 2 (major products) and 1,4,6,7,8,8a-hexahydropyrrolo[2,1-c]-1,2,4-triazines 4b–d, 1,6,7,8,9,9a-hexahydro-4H-pyrido[2,1-c]-1,2,4-triazine 4e, and 1,4,6,7,9,9a-hexahydro-1,4-oxazino[3,4-c]-1,2,4-triazine 4f (minor products).

  2-arylazo-3-(1-azacycloalk-1-yl)-3-methylsulfanylacrylonitriles 与马来酰亚胺在苯中的反应产生了八氢吡咯并[3,4-a]吡咯烷 2a-c、十氢-2,7a-二氮杂环戊并[a]茚 2e 和十氢-5-氧杂-2,7a-二氮杂环戊并[a]茚 2f，这是 1,3-二极环化反应的结果。在与 3-烯丙基硫酰基-2-芳基偶氮-3-(1-氮杂环烷-1-基)丙烯腈 3 的类似反应中，双极环化和分子内环化竞争生成了化合物 2（主要产物）和 1 的混合物、4,6,7,8,8a-六氢吡咯并[2,1-c]-1,2,4-三嗪 4b-d、1,6,7,8,9,9a-六氢-4H-吡啶并[2,1-c]-1,2,4-三嗪 4e 和 1,4,6,7,9,9a-六氢-1,4-恶嗪并[3,4-c]-1,2,4-三嗪 4f 的混合物（次要产物）。