Cargando…

CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles

In this paper, a simple and practical synthesis of benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine tetracyclic heterocycles via a CuI nanoparticle-catalyzed intramolecular C(sp(2))–S coupling reaction is presented. This strategy provides a straightforward method for synthesizing analogs of the...

Descripción completa

Detalles Bibliográficos
Autores principales: Guo, Xiaolong, Wang, Luyao, Hu, Jing, Zhang, Mengmeng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081286/
https://www.ncbi.nlm.nih.gov/pubmed/35541714
http://dx.doi.org/10.1039/c8ra02552e
_version_ 1784702952861073408
author Guo, Xiaolong
Wang, Luyao
Hu, Jing
Zhang, Mengmeng
author_facet Guo, Xiaolong
Wang, Luyao
Hu, Jing
Zhang, Mengmeng
author_sort Guo, Xiaolong
collection PubMed
description In this paper, a simple and practical synthesis of benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine tetracyclic heterocycles via a CuI nanoparticle-catalyzed intramolecular C(sp(2))–S coupling reaction is presented. This strategy provides a straightforward method for synthesizing analogs of the anti-HIV drug 3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182). The reaction rate and yield were increased by employing CuI nanoparticles.
format Online
Article
Text
id pubmed-9081286
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher The Royal Society of Chemistry
record_format MEDLINE/PubMed
spelling pubmed-90812862022-05-09 CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles Guo, Xiaolong Wang, Luyao Hu, Jing Zhang, Mengmeng RSC Adv Chemistry In this paper, a simple and practical synthesis of benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine tetracyclic heterocycles via a CuI nanoparticle-catalyzed intramolecular C(sp(2))–S coupling reaction is presented. This strategy provides a straightforward method for synthesizing analogs of the anti-HIV drug 3,4-dihydro-2H,6H-pyrimido[1,2-c][1,3]benzothiazin-6-imine (PD 404182). The reaction rate and yield were increased by employing CuI nanoparticles. The Royal Society of Chemistry 2018-06-19 /pmc/articles/PMC9081286/ /pubmed/35541714 http://dx.doi.org/10.1039/c8ra02552e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Guo, Xiaolong
Wang, Luyao
Hu, Jing
Zhang, Mengmeng
CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
title CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
title_full CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
title_fullStr CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
title_full_unstemmed CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
title_short CuI nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by S(N)Ar-type C–S, C–N bond formation from isothiocyanatobenzenes and benzimidazoles
title_sort cui nanoparticle-catalyzed synthesis of tetracyclic benzo[e]benzo[4,5]imidazo[1,2-c][1,3]thiazin-6-imine heterocycles by s(n)ar-type c–s, c–n bond formation from isothiocyanatobenzenes and benzimidazoles
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9081286/
https://www.ncbi.nlm.nih.gov/pubmed/35541714
http://dx.doi.org/10.1039/c8ra02552e
work_keys_str_mv AT guoxiaolong cuinanoparticlecatalyzedsynthesisoftetracyclicbenzoebenzo45imidazo12c13thiazin6imineheterocyclesbysnartypecscnbondformationfromisothiocyanatobenzenesandbenzimidazoles
AT wangluyao cuinanoparticlecatalyzedsynthesisoftetracyclicbenzoebenzo45imidazo12c13thiazin6imineheterocyclesbysnartypecscnbondformationfromisothiocyanatobenzenesandbenzimidazoles
AT hujing cuinanoparticlecatalyzedsynthesisoftetracyclicbenzoebenzo45imidazo12c13thiazin6imineheterocyclesbysnartypecscnbondformationfromisothiocyanatobenzenesandbenzimidazoles
AT zhangmengmeng cuinanoparticlecatalyzedsynthesisoftetracyclicbenzoebenzo45imidazo12c13thiazin6imineheterocyclesbysnartypecscnbondformationfromisothiocyanatobenzenesandbenzimidazoles