咪唑并[1,2-a]吡啶-2-羰基叠氮化物 | 421595-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 中文名称: 咪唑并[1,2-a]吡啶-2-羰基叠氮化物
• 英文名称: Imidazo[1,2-a]pyridine-2-carbonyl azide
• 英文别名: imidazo[1,2-a]pyridine-2-carbonyl azide
• CAS: 421595-80-4
• 化学式: C₈H₅N₅O
• 分子量: 187.161
• InChiKey: FKOWRQFHAHOUCP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  咪唑并[1,2-a]吡啶-2-羰基叠氮化物 在 sodium hydroxide 作用下， 反应 10.5h， 生成 咪唑并[1,2-a]吡啶-2-胺
  参考文献：
  名称：

  Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

  摘要：

  In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01141-3
• 作为产物：
  描述：

  咪唑并[1,2-a]吡啶-2-碳酰肼 在 盐酸 、 sodium nitrite 作用下， 反应 4.0h， 以76%的产率得到咪唑并[1,2-a]吡啶-2-羰基叠氮化物
  参考文献：
  名称：

  Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines

  摘要：

  In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(01)01141-3

文献信息

• Aminoimidazo[1,2-a]pyridines: regioselective synthesis of substituted imidazonaphthyridines, azacarbolines and cyclazines
  作者：Jean M Chezal、Emmanuel Moreau、Olivier Chavignon、Vincent Gaumet、Jacques Métin、Yves Blache、Anna Diez、Xavier Fradera、Javier Luque、Jean C Teulade

  DOI：10.1016/s0040-4020(01)01141-3

  日期：2002.1

  In order to study the regioselectivity of thermal cyclocondensation, aminoimidazo [1,2-a]pyridines (AIP) 5a-e were prepared, further converted into iminophosphoranes 7a-e, and ultimately converted regioselectively in angular annulated imidazonaphthyridines (IN) 8a, 10a, 11a, 12a or linear annulated dipyridoimidazole (DPI) 17a. From 2-substituted derivative 23, the peri annulated product 24a was obtained. The starting amines 5a-f reacted with aldehydes to yield regioselectively IN 8a-c, 10a-c, 11a-c, 12a,b, DPI 16a-e, 17a-d and TIBO like structures (+/-)-13 and 24a-c, as proved by X-ray analysis. The 1,2- or 1,4-addition between amines and alpha,beta-unsaturated aldehydes concerning the pyridine and imidazole moieties is discussed in the light of these results. (C) 2002 Published by Elsevier Science Ltd.