2-azido-2'-isocyanatobiphenyl | 221011-27-4

• 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: 2-azido-2'-isocyanatobiphenyl
• 英文别名: 1-Azido-2-(2-isocyanatophenyl)benzene
• CAS: 221011-27-4
• 化学式: C₁₃H₈N₄O
• 分子量: 236.233
• InChiKey: IMGXYCQKGSCPJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-azido-2'-isocyanatobiphenyl 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以5%的产率得到bis<1,3>diazepino>-1,3-diazetidine
  参考文献：
  名称：

  Preparation and Intramolecular Cyclization of Bis(carbodiimides). Synthesis and X-ray Structure of 1,3-Diazetidine-2,4-diimine Derivatives

  摘要：

  Aza-Wittig reactions of bis(iminophosphorane) 1 derived from 2,2'-diazidobiphenyl with aromatic isocyanates provided dibenzo[d,f]-1,3-diazetidino[1,2-a]diazepine derivatives 2 in moderate yields. Similar results can be achieved from the reaction of 2,2'-bis(isothiocyanato)biphenyl 4 with aryliminophosphoranes. Treatment of bis(isothiocyanate) 4 with arylamines and further dehydrosulfurization of the resulting bis(thioureas) leads to the seven-membered ring guanidines 8. N-2-(2'-Azido)biphenyI-N'-arylcarbodiimides 13 react with 1 equiv of triphenylphosphane to give zwitterionic compounds 15, which undergo either hydrolytic cleavage to afford the guanidines 8 or react with 1 equiv of aromatic isocyanates to provide 2. Cross-experiments suggest that the: conversion 15 --> 2 takes place through a nonisolable bis(carbodiimide) that undergoes an intramolecular [2 + 2] cycloaddition at the final step. The reaction of bis(iminophosphorane) 1 with an excess of carbon dioxide leads to a mixture of the tricyclic 1,3-diazetidine derivative 6 and the 14-membered cyclic bis(carbodiimide) 23, which decomposes by thermal treatment. Compound 6 can also be obtained along with the seven-membered cyclic urea derivatives 24 from the reaction of bis(iminophosphorane) 1 with the carbon dioxide source Boc(2)O/DMAP system. A comprehensive mechanistic scheme for the aza-Wittig reactions studied is conveniently presented. The molecular and crystal structures of 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)iminodibenzo[d,f]-1,3-diazetidino-[1,2-a]diazepine (2c) and [a,c]bis[dibenzo[d,f][1,3]diazepino]-1,3]diazepino]-1,3-diazetidine (6) have been determined by X-ray analysis.

  DOI：

  10.1021/jo981339v
• 作为产物：
  描述：

  2-amino-2'-phthalimidobiphenyl 在 盐酸 、 sodium azide 、 一水合肼 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 苯 为溶剂， 反应 10.75h， 生成 2-azido-2'-isocyanatobiphenyl
  参考文献：
  名称：

  Preparation and Intramolecular Cyclization of Bis(carbodiimides). Synthesis and X-ray Structure of 1,3-Diazetidine-2,4-diimine Derivatives

  摘要：

  Aza-Wittig reactions of bis(iminophosphorane) 1 derived from 2,2'-diazidobiphenyl with aromatic isocyanates provided dibenzo[d,f]-1,3-diazetidino[1,2-a]diazepine derivatives 2 in moderate yields. Similar results can be achieved from the reaction of 2,2'-bis(isothiocyanato)biphenyl 4 with aryliminophosphoranes. Treatment of bis(isothiocyanate) 4 with arylamines and further dehydrosulfurization of the resulting bis(thioureas) leads to the seven-membered ring guanidines 8. N-2-(2'-Azido)biphenyI-N'-arylcarbodiimides 13 react with 1 equiv of triphenylphosphane to give zwitterionic compounds 15, which undergo either hydrolytic cleavage to afford the guanidines 8 or react with 1 equiv of aromatic isocyanates to provide 2. Cross-experiments suggest that the: conversion 15 --> 2 takes place through a nonisolable bis(carbodiimide) that undergoes an intramolecular [2 + 2] cycloaddition at the final step. The reaction of bis(iminophosphorane) 1 with an excess of carbon dioxide leads to a mixture of the tricyclic 1,3-diazetidine derivative 6 and the 14-membered cyclic bis(carbodiimide) 23, which decomposes by thermal treatment. Compound 6 can also be obtained along with the seven-membered cyclic urea derivatives 24 from the reaction of bis(iminophosphorane) 1 with the carbon dioxide source Boc(2)O/DMAP system. A comprehensive mechanistic scheme for the aza-Wittig reactions studied is conveniently presented. The molecular and crystal structures of 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)iminodibenzo[d,f]-1,3-diazetidino-[1,2-a]diazepine (2c) and [a,c]bis[dibenzo[d,f][1,3]diazepino]-1,3]diazepino]-1,3-diazetidine (6) have been determined by X-ray analysis.

  DOI：

  10.1021/jo981339v

文献信息

• Preparation and Intramolecular Cyclization of Bis(carbodiimides). Synthesis and X-ray Structure of 1,3-Diazetidine-2,4-diimine Derivatives
  作者：Mateo Alajarín、Pedro Molina、Pilar Sánchez-Andrada、M. Concepción Foces-Foces

  DOI：10.1021/jo981339v

  日期：1999.2.1

  Aza-Wittig reactions of bis(iminophosphorane) 1 derived from 2,2'-diazidobiphenyl with aromatic isocyanates provided dibenzo[d,f]-1,3-diazetidino[1,2-a]diazepine derivatives 2 in moderate yields. Similar results can be achieved from the reaction of 2,2'-bis(isothiocyanato)biphenyl 4 with aryliminophosphoranes. Treatment of bis(isothiocyanate) 4 with arylamines and further dehydrosulfurization of the resulting bis(thioureas) leads to the seven-membered ring guanidines 8. N-2-(2'-Azido)biphenyI-N'-arylcarbodiimides 13 react with 1 equiv of triphenylphosphane to give zwitterionic compounds 15, which undergo either hydrolytic cleavage to afford the guanidines 8 or react with 1 equiv of aromatic isocyanates to provide 2. Cross-experiments suggest that the: conversion 15 --> 2 takes place through a nonisolable bis(carbodiimide) that undergoes an intramolecular [2 + 2] cycloaddition at the final step. The reaction of bis(iminophosphorane) 1 with an excess of carbon dioxide leads to a mixture of the tricyclic 1,3-diazetidine derivative 6 and the 14-membered cyclic bis(carbodiimide) 23, which decomposes by thermal treatment. Compound 6 can also be obtained along with the seven-membered cyclic urea derivatives 24 from the reaction of bis(iminophosphorane) 1 with the carbon dioxide source Boc(2)O/DMAP system. A comprehensive mechanistic scheme for the aza-Wittig reactions studied is conveniently presented. The molecular and crystal structures of 1-(4-methoxyphenyl)-2-(4-methoxyphenyl)iminodibenzo[d,f]-1,3-diazetidino-[1,2-a]diazepine (2c) and [a,c]bis[dibenzo[d,f][1,3]diazepino]-1,3]diazepino]-1,3-diazetidine (6) have been determined by X-ray analysis.