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Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides

The one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: t... Full description

Journal Title: Organic & Biomolecular Chemistry 2012, Vol.10(31), pp.6266-6270
Main Author: Zhao, Fei
Other Authors: Wang, Yang , Zhang, Wen-xiong , Xi, Zhenfeng
Format: Electronic Article Electronic Article
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ID: ISSN: 1477-0520 ; E-ISSN: 1477-0539 ; DOI: 10.1039/c2ob25799h
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recordid: rscc2ob25799h
title: Metal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides
format: Article
creator:
  • Zhao, Fei
  • Wang, Yang
  • Zhang, Wen-xiong
  • Xi, Zhenfeng
subjects:
  • Amines -- Chemistry
  • Carbodiimides -- Chemistry
  • Chlorides -- Chemistry
  • Guanidines -- Chemical Synthesis
  • Oxygen -- Chemistry
ispartof: Organic & Biomolecular Chemistry, 2012, Vol.10(31), pp.6266-6270
description: The one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: to serve as the third component and to activate carbodiimides. In sharp contrast, the AlMe 3 -catalyzed sequential reaction from the same substrates gives the isomer.
language:
source:
identifier: ISSN: 1477-0520 ; E-ISSN: 1477-0539 ; DOI: 10.1039/c2ob25799h
fulltext: fulltext
issn:
  • 1477-0520
  • 1477-0539
  • 14770539
  • 14770520
url: Link


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titleMetal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides
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descriptionThe one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: to serve as the third component and to activate carbodiimides. In sharp contrast, the AlMe 3 -catalyzed sequential reaction from the same substrates gives the isomer.
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subjectAmines -- Chemistry ; Carbodiimides -- Chemistry ; Chlorides -- Chemistry ; Guanidines -- Chemical Synthesis ; Oxygen -- Chemistry;
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titleMetal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides
descriptionThe one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: to serve as the third component and to activate carbodiimides. In sharp contrast, the AlMe 3 -catalyzed sequential reaction from the same substrates gives the isomer.
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atitleMetal-free synthesis of cyclic di-oxoguanidines via one-pot sequential transformation of amines, carbodiimides and acyl dichlorides
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abstractThe one-pot sequential reaction of various amines, carbodiimides, and acyl dichlorides has been achieved for the first time under metal-free conditions to provide symmetric cyclic di-oxoguanidines via an unexpected 2,2-dichloro-imidazolidindione intermediate. Acyl dichlorides have a dual function: to serve as the third component and to activate carbodiimides. In sharp contrast, the AlMe 3 -catalyzed sequential reaction from the same substrates gives the isomer.
doi10.1039/c2ob25799h
pages6266-6270
date2012-07-18