Literature DB >> 25351666

Base-mediated hydroamination of propargylamine: a regioselective intramolecular 5-exo-dig cycloisomerization en route to imidazole-2-thione.

Alok Ranjan1, Ragini Yerande, Prasad B Wakchaure, Swapnil G Yerande, Dattatraya H Dethe.   

Abstract

An intramolecular transition-metal-free base-mediated hydroamination of propargylamine with isothiocyanates has been achieved. This atom-economical, regioselective intramolecular 5-exo-dig cycloisomerization was utilized for the one-pot synthesis of diversely substituted imidazole-2-thione and spiro-cyclic imidazolidine-2-thione. The reaction goes to completion at room temperature via propargylthiourea and 65-97% isolated yields were obtained.

Entities:  

Mesh:

Substances:

Year:  2014        PMID: 25351666     DOI: 10.1021/ol502871r

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  4 in total

1.  Regioselective Base-Mediated Cyclizations of Mono-N-acylpropargylguanidines.

Authors:  Justin M Salvant; Anne V Edwards; Daniel Z Kurek; Ryan E Looper
Journal:  J Org Chem       Date:  2017-06-15       Impact factor: 4.354

2.  Ionic Liquid Solvation versus Catalysis: Computational Insight from a Multisubstituted Imidazole Synthesis in [Et2NH2][HSO4].

Authors:  Yusif Abdullayev; Vagif Abbasov; Lucas C Ducati; Avtandil Talybov; Jochen Autschbach
Journal:  ChemistryOpen       Date:  2016-08-17       Impact factor: 2.911

3.  Biradical o-iminobenzosemiquinonato(1-) complexes of nickel(ii): catalytic activity in three-component coupling of aldehydes, amines and alkynes.

Authors:  Mina Nasibipour; Elham Safaei; Ali Moaddeli; Marziyeh Sadat Masoumpour; Andrzej Wojtczak
Journal:  RSC Adv       Date:  2021-04-06       Impact factor: 3.361

4.  Identification of two novel thiazolidin-2-imines as tyrosinase inhibitors: synthesis, crystal structure, molecular docking and DFT studies.

Authors:  Syeda Aaliya Shehzadi; Aamer Saeed; Fouzia Perveen; Pervaiz Ali Channar; Ifzan Arshad; Qamar Abbas; Saima Kalsoom; Sammer Yousaf; Jim Simpson
Journal:  Heliyon       Date:  2022-08-11
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.