Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles

Research output

5 Citations (Scopus)

Abstract

An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.

Original languageEnglish
Pages (from-to)11232-11244
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number18
DOIs
Publication statusPublished - 21 Sep 2018

Fingerprint

Oxadiazoles
Imidazoles
Derivatives
Triazoles
1-sulfonyl-1,2,3-triazole
alkoxyl radical

Scopus subject areas

  • Organic Chemistry

Cite this

@article{c8c9937bb98543fda3ed6cc6c9faa862,
title = "Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles: Regioselective Synthesis of 5-Sulfonamidoimidazoles",
abstract = "An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.",
author = "Strelnikova, {Julia O.} and Rostovskii, {Nikolai V.} and Starova, {Galina L.} and Khlebnikov, {Alexander F.} and Novikov, {Mikhail S.}",
year = "2018",
month = "9",
day = "21",
doi = "10.1021/acs.joc.8b01809",
language = "English",
volume = "83",
pages = "11232--11244",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "18",

}

TY - JOUR

T1 - Rh(II)-Catalyzed Transannulation of 1,2,4-Oxadiazole Derivatives with 1-Sulfonyl-1,2,3-triazoles

T2 - Regioselective Synthesis of 5-Sulfonamidoimidazoles

AU - Strelnikova, Julia O.

AU - Rostovskii, Nikolai V.

AU - Starova, Galina L.

AU - Khlebnikov, Alexander F.

AU - Novikov, Mikhail S.

PY - 2018/9/21

Y1 - 2018/9/21

N2 - An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.

AB - An effective method for the synthesis of fully substituted 5-sulfonamidoimidazoles by Rh(II)-catalyzed transannulation of 1,2,4-oxadiazole derivatives with N-sulfonyl-1,2,3-triazoles is reported. The reaction works well with both aromatic 1,2,4-oxadiazoles and 1,2,4-oxadiazol-5-ones providing a flexible approach to N-(alkoxy/amino)carbonyl- and N-alkyl-substituted imidazoles. Both the disclosed reactions are completely regioselective and provide the first examples of a carbenoid-mediated transformation of N,N,O-heterocycles.

UR - http://www.scopus.com/inward/record.url?scp=85052327905&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b01809

DO - 10.1021/acs.joc.8b01809

M3 - Article

AN - SCOPUS:85052327905

VL - 83

SP - 11232

EP - 11244

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 18

ER -