Literature DB >> 26934455

Rhodium(II)-Catalyzed and Thermally Induced Intramolecular Migration of N-Sulfonyl-1,2,3-triazoles: New Approaches to 1,2-Dihydroisoquinolines and 1-Indanones.

Run Sun1, Yu Jiang1, Xiang-Ying Tang2, Min Shi3,4.   

Abstract

New rhodium(II)-catalyzed or thermally induced intramolecular alkoxy group migration of N-sulfonyl-1,2,3-triazoles has been developed, affording divergent synthesis of 1,2-dihydroisoquinoline and 1-indanone derivatives according to different conditions. N-Sulfonyl keteneimine is the key intermediate for the synthesis of dihydroisoquinoline, whereas the aza-vinyl carbene intermediate results in the formation of 1-indanone.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  carbenes; heterocycles; rearrangement; rhodium; triazoles

Year:  2016        PMID: 26934455     DOI: 10.1002/chem.201504914

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  4 in total

Review 1.  Synthesis of 1-indanones with a broad range of biological activity.

Authors:  Marika Turek; Dorota Szczęsna; Marek Koprowski; Piotr Bałczewski
Journal:  Beilstein J Org Chem       Date:  2017-03-09       Impact factor: 2.883

2.  Intramolecular azavinyl carbene-triggered rearrangement of furans.

Authors:  Anton S Makarov; Maxim G Uchuskin; A Stephen K Hashmi
Journal:  Chem Sci       Date:  2019-07-26       Impact factor: 9.825

3.  A facile metal-free one-pot synthesis of 3-aminoisoquinolines by intramolecular transannulation of 1-sulfonyl-4-(2-aminomethylphenyl)-1,2,3-triazoles.

Authors:  Hai Shang; Ling-Yu Li; Yu Tian; Hong-Mei Jia; Zhong-Mei Zou
Journal:  RSC Adv       Date:  2020-10-28       Impact factor: 4.036

4.  Diversity-oriented synthesis of heterocycles and macrocycles by controlled reactions of oxetanes with α-iminocarbenes.

Authors:  Alejandro Guarnieri-Ibáñez; Florian Medina; Céline Besnard; Sarah L Kidd; David R Spring; Jérôme Lacour
Journal:  Chem Sci       Date:  2017-06-12       Impact factor: 9.825

  4 in total

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