Rhodium(II)-Catalyzed Formal [3 + 2] Cycloaddition of N‑Sulfonyl-1,2,3-triazoles with Isoxazoles: Entry to Polysubstituted 3‑Aminopyrroles

A novel rhodium­(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from termin...

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Published inOrganic letters Vol. 17; no. 21; pp. 5224 - 5227
Main Authors Lei, Xiaoqiang, Li, Longbo, He, Yu-Peng, Tang, Yefeng
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.11.2015
Amer Chemical Soc
Subjects
alkynes
azides
chemical structure
Chemistry
Chemistry, Organic
cycloaddition reactions
Physical Sciences
rhodium
Science & Technology
synthesis
2H-AZIRINES
AZIDES
SCOPE
1,2,3-TRIAZOLES
DIVERGENT SYNTHESIS
REACTIVITY
TERMINAL ALKYNES
TRANSANNULATION
PYRROLES
CATALYST
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Summary:A novel rhodium­(II)-catalyzed formal [3 + 2] cycloaddition of N-sulfonyl-1,2,3-triazoles with isoxazoles has been achieved that provides an efficient method for the synthesis of polysubstituted 3-aminopyrrole derivatives. An operationally simple one-pot synthesis of the titled compounds from terminal alkynes, tosyl azide, and isoxazoles was also developed. The presented reaction affords an illustrative example of employing 1,2,3-triazoles as the [2C]-component in relevant cycloaddition reactions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.5b02570