Cargando…
Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes
Rhodium catalyzed synthesis of substituted tetrahydropyridines was accomplished from readily accessible thio-tethered N-sulfonyl-1,2,3-triazoles. The reaction involves tandem rhodium catalyzed 1,2-sulfur migration in β-thio-α-diazoimines, generated from thio-tethered N-sulfonyl-1,2,3-triazoles, to t...
Autores principales: | , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2015
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5950192/ https://www.ncbi.nlm.nih.gov/pubmed/29861910 http://dx.doi.org/10.1039/c5sc02379c |
_version_ | 1783322841014337536 |
---|---|
author | Yadagiri, Dongari Anbarasan, Pazhamalai |
author_facet | Yadagiri, Dongari Anbarasan, Pazhamalai |
author_sort | Yadagiri, Dongari |
collection | PubMed |
description | Rhodium catalyzed synthesis of substituted tetrahydropyridines was accomplished from readily accessible thio-tethered N-sulfonyl-1,2,3-triazoles. The reaction involves tandem rhodium catalyzed 1,2-sulfur migration in β-thio-α-diazoimines, generated from thio-tethered N-sulfonyl-1,2,3-triazoles, to thio-substituted 1-azadiene and subsequent self aza-Diels–Alder reaction. Interestingly, the methodology was effectively extended to the synthesis of fused tetrahydropyridines, dihydropyridines and cyclohexenes through the in situ trapping of the intermediate, 1-azadiene, with various dienophiles such as enol ether, enamine, ketene S,S-acetal, alkyne, alkene and diene. Furthermore, the direct conversion of propargyl sulfides to (fused)-tetrahydropyridines was also achieved through the successful integration of copper and rhodium catalysts in one-pot. |
format | Online Article Text |
id | pubmed-5950192 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-59501922018-06-01 Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes Yadagiri, Dongari Anbarasan, Pazhamalai Chem Sci Chemistry Rhodium catalyzed synthesis of substituted tetrahydropyridines was accomplished from readily accessible thio-tethered N-sulfonyl-1,2,3-triazoles. The reaction involves tandem rhodium catalyzed 1,2-sulfur migration in β-thio-α-diazoimines, generated from thio-tethered N-sulfonyl-1,2,3-triazoles, to thio-substituted 1-azadiene and subsequent self aza-Diels–Alder reaction. Interestingly, the methodology was effectively extended to the synthesis of fused tetrahydropyridines, dihydropyridines and cyclohexenes through the in situ trapping of the intermediate, 1-azadiene, with various dienophiles such as enol ether, enamine, ketene S,S-acetal, alkyne, alkene and diene. Furthermore, the direct conversion of propargyl sulfides to (fused)-tetrahydropyridines was also achieved through the successful integration of copper and rhodium catalysts in one-pot. Royal Society of Chemistry 2015-10-01 2015-07-10 /pmc/articles/PMC5950192/ /pubmed/29861910 http://dx.doi.org/10.1039/c5sc02379c Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Yadagiri, Dongari Anbarasan, Pazhamalai Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes |
title | Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes
|
title_full | Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes
|
title_fullStr | Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes
|
title_full_unstemmed | Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes
|
title_short | Tandem 1,2-sulfur migration and (aza)-Diels–Alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes
|
title_sort | tandem 1,2-sulfur migration and (aza)-diels–alder reaction of β-thio-α-diazoimines: rhodium catalyzed synthesis of (fused)-polyhydropyridines, and cyclohexenes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5950192/ https://www.ncbi.nlm.nih.gov/pubmed/29861910 http://dx.doi.org/10.1039/c5sc02379c |
work_keys_str_mv | AT yadagiridongari tandem12sulfurmigrationandazadielsalderreactionofbthioadiazoiminesrhodiumcatalyzedsynthesisoffusedpolyhydropyridinesandcyclohexenes AT anbarasanpazhamalai tandem12sulfurmigrationandazadielsalderreactionofbthioadiazoiminesrhodiumcatalyzedsynthesisoffusedpolyhydropyridinesandcyclohexenes |