60006-16-8

Upstream product

• 110-91-8 morpholine 
• 622-16-2 1,3-Diphenylcarbodiimide 
• 103-72-0 phenyl isothiocyanate 
• 62-53-3 aniline 
• 1527-91-9 N-phenylbenzamidine 
• 4559-92-6 N-phenylmorpholine-4-carboxamide 
• 103-71-9 phenyl isocyanate 
• 30543-38-5 N-phenyl-1-morpholinecarbimidoyl chloride 
• 102-08-9 N,N-diphenylthiourea 

Relevant academic research and scientific papers

De novodesign and synthesis of dipyridopurinone derivatives as visible-light photocatalysts in productive guanylation reactions

Described here is thede novodesign and synthesis of a series of 6H-dipyrido[1,2-e:2′,1′-i]purin-6-ones (DPs) as a new class of visible-light photoredox catalysts (PCs). The synthesizedDP1-5showed theirλAbs(max)values in 433-477 nm, excited state redox potentials in 1.15-0.69 eV and ?1.41 to ?1.77 eV (vs.SCE), respectively. As a representative,DP4enables the productive guanylation of various amines, including 1°, 2°, and 3°-alkyl primary amines, secondary amines, aryl and heteroaryl amines, amino-nitrile, amino acids and peptides as well as propynylamines and α-amino esters giving diversities in biologically important guanidines and cyclic guanidines. The photocatalytic efficacy ofDP4in the guanylation overmatched commonly used Ir and Ru polypyridyl complexes, and some organic PCs. Other salient merits of this method include broad substrate scope and functional group tolerance, gram-scale synthesis, and versatile late-stage derivatizations that led to a derivative81exhibiting 60-fold better anticancer activity against Ramos cells with the IC50of 0.086 μM than that of clinical drug ibrutinib (5.1 μM).

A Mild Photocatalytic Synthesis of Guanidine from Thiourea under Visible Light

In this work, we developed the catalytic guanylation of thiourea using Ru(bpy)3Cl2 as a photocatalyst under irradiation by visible light. The conversion of various thioureas to the corresponding guanidines was achieved using 1-5 mol % of photocatalyst in a mixture of water and ethanol at room temperature. Key benefits of this reaction include the use of photoredox catalyst, low-toxicity solvents/base, ambient temperature, and an open-flask environment.

Ph3P/I2-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates

A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2 system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.

Guanidine Synthesis: Use of Amidines as Guanylating Agents

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.

Electronic Activity Tuning of Acyclic Guanidines for Lactide Polymerization

Novel aromatic guanidine-based organocatalysts for the ring-opening of l-lactide were synthesized and applied in comprehensive polymerization experiments and kinetic studies. The introduction of electronically active substituents led to a significant chan

Design and synthesis of a photoswitchable guanidine catalyst

A novel design as well as a straight-forward synthesis for a photoswitchable guanidine catalyst is reported. Intense studies of the photochromic properties demonstrated the reversible switchability of its photosensitive azobenzene moiety. Its activity in

Role of quaternaryammonium permanganates in the synthesis of substituted guanidines - A comparative study

Quaternaryammonium permanganate transforms 1,3-diarylthioureas in the presence of an amine to the respective trisubstituted guanidines in excellent yields.

A Short and Concise Synthesis of Guanidines

A facile high yielding process of guanidines is reported by reaction of amine nucleophiles on the oxidised thioureas in an aqueous medium using the unexploited reagents sodium chlorite and sodium metaperiodate for the oxidation of 1,3-disubstituted thioureas.

Lac sulfur on alumina-triethanolamine - An effective reagent for the synthesis of substituted guanidines

A direct synthesis of substituted guanidines is reported from their thiourea analogues. The strategy adopted is a concise approach to the synthesis of the title compounds.