Literature DB >> 24839200

Rhodium(II)-catalyzed intramolecular cycloisomerizations of methylenecyclopropanes with N-sulfonyl 1,2,3-triazoles.

Kai Chen1, Zi-Zhong Zhu, Yong-Sheng Zhang, Xiang-Ying Tang, Min Shi.   

Abstract

A novel rhodium(II)-catalyzed tandem cycloisomerization of methylenecyclopropanes (MCPs) with N-sulfonyl 1,2,3-triazoles is disclosed. The reaction produces a series of highly functionalized polycyclic N heterocycles via a rhodium imino carbene intermediate. A distinct feature of this divergent synthesis is that different types of substrates control the reaction pathways. Moreover, several interesting transformations of these products to construct diazabicyclo[3.2.1]octane derivatives are also reported.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbenes; isomerization; nitrogen heterocycles; rhodium; small ring systems

Year:  2014        PMID: 24839200     DOI: 10.1002/anie.201402803

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  4 in total

1.  Scope of the Reactions of Indolyl- and Pyrrolyl-Tethered N-Sulfonyl-1,2,3-triazoles: Rhodium(II)-Catalyzed Synthesis of Indole- and Pyrrole-Fused Polycyclic Compounds.

Authors:  Liangbing Fu; Huw M L Davies
Journal:  Org Lett       Date:  2017-03-30       Impact factor: 6.005

2.  Light-induced metal-free transformations of unactivated pyridotriazoles.

Authors:  Ziyan Zhang; Dongari Yadagiri; Vladimir Gevorgyan
Journal:  Chem Sci       Date:  2019-07-25       Impact factor: 9.825

3.  Efficient synthesis of cyclic amidine-based fluorophores via 6π-electrocyclic ring closure.

Authors:  Guofeng Li; Man Zhao; Junqiu Xie; Ying Yao; Lingyun Mou; Xiaowei Zhang; Xiaomin Guo; Wangsheng Sun; Zheng Wang; Jiecheng Xu; Jianzhong Xue; Tao Hu; Ming Zhang; Min Li; Liang Hong
Journal:  Chem Sci       Date:  2020-03-13       Impact factor: 9.825

4.  Copper-catalyzed asymmetric cyclization of alkenyl diynes: method development and new mechanistic insights.

Authors:  Xin-Qi Zhu; Pan Hong; Yan-Xin Zheng; Ying-Ying Zhen; Feng-Lin Hong; Xin Lu; Long-Wu Ye
Journal:  Chem Sci       Date:  2021-06-11       Impact factor: 9.825

  4 in total

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