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

被引：1

作者：

Nutt, Michael J. ^{[1
]}

Annear, Jack W. ^{[1
]}

Jones, Kieran D. ^{[1
]}

Flematti, Gavin R. ^{[1
]}

Moggach, Stephen A. ^{[1
]}

Stewart, Scott G. ^{[1
]}

机构：

[1] Univ Western Australia M310, Sch Mol Sci, Crawley, WA 6009, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 16期

关键词：

NITROGEN-HETEROCYCLES; TERMINAL ALKYNES; PYRAZINE DERIVATIVES; SULFONYL AZIDES; H INSERTION; 1,2,3-TRIAZOLES; HYDROGENATION; REACTIVITY; CYCLOADDITIONS; REARRANGEMENTS;

D O I：

10.1021/acs.joc.3c01259

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Thedirhodium(II)-catalyzed synthesis of a range of C2-substituted2,3-dehydropiperazines using 1-mesyl-1,2,3-triazoles and & beta;-haloalkylcarbamatesis reported. The reaction is proposed to proceed through an & alpha;-iminorhodium carbene 1,3-insertion into N-H followed by a base-mediatedcyclization. C-Substituted dehydropiperazines can also be conducteddirectly from terminal alkynes in a three-step, one-pot operation,forming the triazole in situ. This methodology hasalso been expanded to afford several 2,5-disubstituted 2,3-dehydropiperazinesas well as a larger 4,5,6,7-tetrahydro-1H-1,4-diazepinederivative.

引用

页码：11968 / 11979

页数：12

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