Dirhodium-Catalyzed Transannulation of N‑Sulfonyl-1,2,3-triazoles to 2,3-Dehydropiperazines

The dirhodium­(II)-catalyzed synthesis of a range of C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. The reaction is proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N–H followed by a base-mediated cyclization. C-Sub...

Full description

Saved in:
Bibliographic Details
Published inJournal of organic chemistry Vol. 88; no. 16; pp. 11968 - 11979
Main Authors Nutt, Michael J., Annear, Jack W., Jones, Kieran D., Flematti, Gavin R., Moggach, Stephen A., Stewart, Scott G.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.08.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
HYDROGENATION
NITROGEN-HETEROCYCLES
PYRAZINE DERIVATIVES
SULFONYL AZIDES
1,2,3-TRIAZOLES
CYCLOADDITIONS
REACTIVITY
TERMINAL ALKYNES
H INSERTION
REARRANGEMENTS
Online AccessGet full text

Cover

More Information
Summary:The dirhodium­(II)-catalyzed synthesis of a range of C2-substituted 2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and β-haloalkylcarbamates is reported. The reaction is proposed to proceed through an α-imino rhodium carbene 1,3-insertion into N–H followed by a base-mediated cyclization. C-Substituted dehydropiperazines can also be conducted directly from terminal alkynes in a three-step, one-pot operation, forming the triazole in situ. This methodology has also been expanded to afford several 2,5-disubstituted 2,3-dehydropiperazines as well as a larger 4,5,6,7-tetrahydro-1H-1,4-diazepine derivative.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01259