3-allylsulfanyl-2-[(4-nitrophenyl)azo]-3-(1-piperidyl)prop-2-enenitrile | 1258406-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-allylsulfanyl-2-[(4-nitrophenyl)azo]-3-(1-piperidyl)prop-2-enenitrile
• CAS: 1258406-71-1
• 化学式: C₁₇H₁₉N₅O₂S
• 分子量: 357.436
• InChiKey: QIPFZFNDVXKNIJ-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-甲基马来酰亚胺 、 3-allylsulfanyl-2-[(4-nitrophenyl)azo]-3-(1-piperidyl)prop-2-enenitrile 以 苯 为溶剂， 反应 1.5h， 以50%的产率得到
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides

  摘要：

  A series of 1,2-diaza-1,3-butadienes with terminal S,N-acetal function were obtained and reacted with N-methyl- and N-phenylmaleimides. As a result of the 1,3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1H-pyrrolo[3,4-a]indolizine, octahydropyrrolo[3',4':3,4]pyrrolo[1,2-a]azepine, hexahydropyrrolo[3',41:3,4]pyrrolo[2,1-c][1,4]oxazine and -thiazine, were obtained with good yields in mild conditions. Experimental and theoretic results allowed establishment of a relationship between the structures of the tert-cycloallcylamine group and the activity of the azomethine ylides generated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.087
• 作为产物：
  描述：

  、 3-溴丙烯 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到3-allylsulfanyl-2-[(4-nitrophenyl)azo]-3-(1-piperidyl)prop-2-enenitrile
  参考文献：
  名称：

  1,3-Dipolar cycloaddition of 3-alkylsulfanyl-2-arylazo-3-(tert-cycloalkylamino)acrylonitriles with N-methyl- and N-phenylmaleimides

  摘要：

  A series of 1,2-diaza-1,3-butadienes with terminal S,N-acetal function were obtained and reacted with N-methyl- and N-phenylmaleimides. As a result of the 1,3-dipolar cycloaddition, a range of new functionalized nonaromatic heterocyclic compounds including: octahydro-1H-pyrrolo[3,4-a]indolizine, octahydropyrrolo[3',4':3,4]pyrrolo[1,2-a]azepine, hexahydropyrrolo[3',41:3,4]pyrrolo[2,1-c][1,4]oxazine and -thiazine, were obtained with good yields in mild conditions. Experimental and theoretic results allowed establishment of a relationship between the structures of the tert-cycloallcylamine group and the activity of the azomethine ylides generated. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.087

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）。