56499-93-5Relevant academic research and scientific papers
Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions
Srisa, Jakkrit,Tankam, Theeranon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
supporting information, p. 3335 - 3343 (2019/09/12)
In this work, we developed a one-pot synthesis of guanidine directly from isothiocyanate using DIB (diacetoxyiodobenzene) as a desulfurizing agent under micellar conditions in water. Our optimization study revealed that the use of 1 % TPGS-750-M as a surfactant with NaOH as an additive base at room temperature can convert a variety of isothiocyanates and amines into corresponding guanidines in excellent yields (69–95 %). This synthetic process in water can be applied to prepare guanidine at gram-scale quantity. Our aqueous micellar medium also demonstrated high reusability as the reaction can be performed for several cycles without losing its efficiency. The reaction is metal-free, utilizes water as solvent and practical (room temperature and open flask).
Guanidine Synthesis: Use of Amidines as Guanylating Agents
Baeten, Mattijs,Maes, Bert U. W.
supporting information, p. 826 - 833 (2016/03/12)
The use of amidines for the tandem or one-pot synthesis of guanidines is reported. Guanidines are obtained by oxidative rearrangement of readily available and stable amidines into carbodiimides, followed by in situ reaction with amines. The protocol can be executed under mild reaction conditions (30°C), in a green solvent (dimethyl carbonate). The amine scope is broad, including sterically hindered, oxidation-sensitive and chiral amines. Examples for the synthesis of both acyclic and cyclic guanidines are provided. 2-Propoxyphenyl iodide (2-PrOPhI) by-product, generated from the oxidant [N-(p-toluenesulfonyl)imino](2-propoxyphenyl)iodinane (2-PrOPhINTs), can be isolated in high yields making regeneration of the hypervalent iodine reagent possible. The utility and greenness of the synthetic method versus the state-of-the-art is demonstrated by a new route towards the antihypertensive drug Pinacidil. The process mass intensity (PMI) of the new route is only 24% of the classical one.
Palladium-catalyzed cross-coupling reaction of azides with isocyanides
Zhang, Zhen,Li, Zongyang,Fu, Bin,Zhang, Zhenhua
, p. 16312 - 16315 (2015/11/16)
An efficient palladium-catalyzed cross-coupling reaction of azides with isocyanides is developed, providing a general synthetic route to unsymmetric carbodiimides with excellent yields. This method shows a broad substrate scope, including not only aryl azides, but also unactivated benzyl and alkyl azides. Furthermore, from readily available substrates, Pd-catalyzed coupling with a tandem amine insertion cascade to obtain unsymmetric trisubstituted guanidines has been achieved in a one-pot fashion.
Application of α-chloroaldoxime O-methanesulfonates to one-pot synthesis of N,N′,N″-substituted guanidines via Tiemann rearrangement
Yamamoto, Yuhei,Mizuno, Hiroo,Tsuritani, Takayuki,Mase, Toshiaki
scheme or table, p. 5813 - 5815 (2009/12/26)
A practical one-pot synthesis of N,N′,N″-trisubstituted guanidines via Tiemann rearrangement involving the reaction of α-chloroaldoxime O-methanesulfonates with alkyl amines is disclosed.
