75358-30-4Relevant academic research and scientific papers
The synthesis of 2-amino-4(3H)-quinazolinones and related heterocycles via a mild electrocyclization of aryl guanidines
Sales, Zachary S.,Mani, Neelakandha S.,Allison, Brett D.
supporting information, p. 1623 - 1626 (2018/03/29)
A new method for the preparation of 2-amino-4(3H)-quinazolinones and similar fused heterocycles is described. Simply warming a mixture of an aryl guanidine and carbonyl diimidazole in acetonitrile results in formation of a putative N-amidinoisocyanate intermediate which undergoes a 6π-electron electrocyclic reaction with the aryl ring to generate the quinazolinone ring system. The mild conditions are compatible with a variety of functional groups, and the reaction is shown to be successful on multigram scale.
Copper(i) iodide-catalyzed synthesis of N,N′-disubstituted guanidines from n-substituted cyanamides
Zeng, Cian-Jhe,Chen, Chia-Jung,Chang, Chih-Wei,Chen, Hui-Ting,Chien, Tun-Cheng
, p. 1134 - 1137 (2014/08/05)
A facile and effective synthesis of N-alkyl-N′-arylguanidines was accomplished by the reaction of N-arylcyanamides with various primary and secondary alkylamines, under the catalysis of copper(i) iodide and Xantphos in DMF. This methodology provides a direct access to versatile N,N′- disubstituted guanidine derivatives from N-arylcyanamides that can be readily prepared from the corresponding nitriles via Tiemann rearrangement. CSIRO 2014.
CuI-catalyzed amination of arylhalides with guanidines or amidines: A facile synthesis of 1-H-2-substituted benzimidazoles
Deng, Xiaohu,McAllister, Heather,Mani, Neelakandha S.
supporting information; experimental part, p. 5742 - 5745 (2009/12/06)
(Figure Presented) CuI/L5 (N,N′-dimethylethylenediamine) proves to be an efficient catalyst system for the amination of arylhalides with guanidines. The same catalyst system is then successfully applied to the one-step synthesis of 1-H-2-aminobenzimidazol
