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

作者: Fei Zhao , Yang Wang , Wen-Xiong Zhang , Zhenfeng Xi

DOI: 10.1039/C2OB25799H

关键词:

摘要: 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 have a dual function: serve as third component activate carbodiimides. In sharp contrast, AlMe3-catalyzed from same substrates gives isomer.

参考文章(73)
Tanja Gaich, Phil S. Baran, Aiming for the Ideal Synthesis Journal of Organic Chemistry. ,vol. 75, pp. 4657- 4673 ,(2010) , 10.1021/JO1006812
Masayoshi Nishiura, Zhaomin Hou, Half-Sandwich Rare Earth Metal Complexes as Novel Catalysts for Olefin Polymerization and Other Chemical Transformations Bulletin of the Chemical Society of Japan. ,vol. 83, pp. 595- 608 ,(2010) , 10.1246/BCSJ.20100003
C. M. Baltzer, C. G. McCarty, Synthesis of cyclic N-cyanoguanidines Journal of Organic Chemistry. ,vol. 38, pp. 155- 156 ,(1973) , 10.1021/JO00941A035
Hongbin Li, Jeffrey L. Petersen, Kung K. Wang, Cascade cyclizations via N,4-didehydro-2-(phenylamino)pyridine biradicals/zwitterions generated from enyne-carbodiimides. Journal of Organic Chemistry. ,vol. 68, pp. 5512- 5518 ,(2003) , 10.1021/JO020760N
Zitao Wang, Yang Wang, Wen-Xiong Zhang, Zhaomin Hou, Zhenfeng Xi, Efficient one-pot synthesis of 2,3-dihydropyrimidinthiones via multicomponent coupling of terminal alkynes, elemental sulfur, and carbodiimides. Journal of the American Chemical Society. ,vol. 131, pp. 15108- 15109 ,(2009) , 10.1021/JA9069419
Shigeki Matsunaga, Richard E. Moore, Walter P. Niemczura, Wayne W. Carmichael, Anatoxin-a(s), a potent anticholinesterase from Anabaena flos-aquae Journal of the American Chemical Society. ,vol. 111, pp. 8021- 8023 ,(1989) , 10.1021/JA00202A057
George Buchi, Abimael D. Rodriguez, Kenichi Yakushijin, Syntheses of (.+-.)-alchorneine and (.+-.)-isoalchorneine Journal of Organic Chemistry. ,vol. 54, pp. 4494- 4496 ,(1989) , 10.1021/JO00280A009
Mihyong Kim, John V. Mulcahy, Christine G. Espino, J. Du Bois, Expanding the Substrate Scope for C−H Amination Reactions: Oxidative Cyclization of Urea and Guanidine Derivatives Organic Letters. ,vol. 8, pp. 1073- 1076 ,(2006) , 10.1021/OL052920Y
Gerwalt Zinner, Rüudiger Vollrath, Addition bifunktioneller Carbonsäurechloride an Carbodiimide und einige Folgereaktionen Chemische Berichte. ,vol. 103, pp. 766- 776 ,(1970) , 10.1002/CBER.19701030316