Synthesis of α-amino amidines through molecular iodine-catalyzed three-component coupling of isocyanides, aldehydes and amines

Abstract

SummaryA facile and efficient synthetic protocol for the synthesis of α-amino amidines has been developed using a molecular iodine-catalyzed three-component coupling reaction of isocyanides, amines, and aldehydes. The presented strategy offers the advantages of mild reaction conditions, low environmental impact, clean and simple methodology, high atom economy, wide substrate scope and high yields.

Transition Metal Ions Regulated Structural and Catalytic Behaviors of Coordination Polymers

“…The Ag + ion has distorted tetrahedral geometry (AgO 2 N 2 ) connecting two oxygen atoms carboxylate group, one nitrogen atom of pyrazolate ligand, and one nitrogen atom of solvent moiety (Figure a and Figure S12). The respective bond lengths of Ag–O fall in the range 2.337(3)–2.481(3) Å, and Ag–N bond distances are in the range 2.237(5)–2.302(4) Å, closely matching with the earlier reported silver­(I)-based coordination compounds. ,− The various < O/N–Ag–O/N angles differ in the range 84.66(11)–133.69(17)° with an average of 109.03°, confirming the distorted tetrahedral geometry of the Ag ion. The important bond lengths and angles are supplied in Table S3.…”

“…Recently, MCRs have appeared as valuable tools for the synthesis of heterocyclic molecules and drug intermediates in academia and industry . The synthesis of α-amino amidine and its derivatives is one of the important and promising classes of MCRs due to their potential biological applications such as biosynthesis of purines, non-vaccine derivatives, antimuscarinic agents, and iminopeptides, synthesis of antibiotics, and modulation of their thermodynamic and pharmacokinetic profile. , Very few reports are available for the multicomponent α-amino amidine formation reaction catalyzed through the homogeneous or heterogeneous catalysts, but CPs/MOFs catalyzed MCR for α-amino amidine formation are not investigated so far . Therefore, we are keen to focus on coordination-environment- and crystal-structure-dependent Lewis acid mediated MCR for employing newly designed CPs.…”

Substituted, Fused, Tricyclic 6,7‐Dihydro‐1H,5H‐pyrido[1,2,3‐de]quinoxaline‐3‐amines by Isocyanide‐Abetted Cycloaddition Reaction

“…Iodine has already been used for Ugi and GBB reactions, but it failed to provide desired compound 5 . However, Schiff base 5a and amide 5aa were isolated in yields of 62 and 32 %, respectively (Table , entry 8) Similar results were observed for ZnCl 2 , SnCl 2 · 2H 2 O, InCl 3 , and CeCl 3 · 7H 2 O, all of which led to the formation of amide 5aa along with Schiff base 5a (Table , entries 9 to 12). The yield of the Schiff base was not determined, and its formation was confirmed by TLC analysis.…”

The Ugi Three‐Component Reaction; a Valuable Tool in Modern Organic Synthesis

“…Another valuable catalytic option towards α-aminoamidines 64 is molecular iodine as a catalyst suggested in 2014 by Maurya et al [147] With a catalytic quantity of only 1 mol-% and a mild, inexpensive and efficient catalytic protocol included, the formation of α-aminoamidine was observed (75-91 %) with a wide range of starting materials being used (Scheme 38).…”