56497-11-1Relevant academic research and scientific papers
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.
O-Iodoxybenzoic acid mediated oxidative condensation: Synthesis of guanidines using 1,-3-disubstituted thiourea precursors
Dangate, Prasad S.,Akamanchi, Krishnacharya G.
, p. 6765 - 6767 (2013/01/15)
An efficient and mild oxidative condensation procedure using o-iodoxybenzoic acid and triethylamine or ammonia as base has been developed for the synthesis of guanidines starting from easily synthesizable 1,3-disubstituted thioureas and amines or ammonia.
Direct guanidinylation of aryl and heteroaryl halides via copper-catalyzed cross-coupling reaction
Hammoud, Hassan,Schmitt, Martine,Bihel, Frederic,Antheaume, Cyril,Bourguignon, Jean-Jacques
scheme or table, p. 417 - 423 (2012/03/09)
A modified Ullmann reaction using p-methoxybenzyl (PMB) guanidine as guanidinylation agent yielded various aryl and heteroaryl guanidines in good yields.
A highly efficient method for the synthesis of guanidinium derivatives
Manimala, Joseph C,Anslyn, Eric V
, p. 565 - 567 (2007/10/03)
A high yielding synthesis of guanidiniums with the use of the ethyl carbamate protecting group is presented. This strategy eliminates many steric hindrance and electronic problems. The deprotection of the products by Me3SiBr is also demonstrated.
Novel linker for the solid-phase synthesis of guanidines
Josey, John A.,Tarlton, Catherine A.,Payne, Courtney E.
, p. 5899 - 5902 (2007/10/03)
A novel linker for the generation of alkyl-, acyl- and arylguanidines as an attachment point in solid phase synthesis has been developed. Introduction of a suitably functionalized thiourea to Wang resin via a carbamate linkage, followed by displacement of sulfur with a 1°or 2°amine affords resin bound guanidines suitably protected for further manipulation. Activation of the thiourea with Mukaiyama's reagent allows for the generation of arylguanidines. Mild acid treatment effects deprotection and liberation from the resin to afford guanidines in good yield and high purity.
