Synthesis 2019; 51(12): 2506-2514
DOI: 10.1055/s-0037-1611795
special topic
© Georg Thieme Verlag Stuttgart · New York

Ruthenium-Catalyzed Annulation of N-Cbz Hydrazones via C–H/N–N Bond Activation for the Rapid Synthesis of Isoquinolines

Dewal S. Deshmukh
,
Bhalchandra M. Bhanage*
Department of Chemistry, Institute of Chemical Technology, N. Parekh Marg, Matunga, Mumbai 400 019, India   Email: bm.bhanage@gmail.com   Email: bm.bhanage@ictmumbai.edu.in
› Author Affiliations
The author D. S. D. would like to thank the University Grants Commission (UGC), New Delhi, India for providing a Senior Research Fellowship under Basic Science Research (BSR) scheme [F.25-1/2014-15, F.7-227/2009, 16th Feb 2015].
Further Information

Publication History

Received: 26 February 2019

Accepted: 19 March 2019

Publication Date:
10 April 2019 (online)

Published as part of the Special Topic Ruthenium in Organic Synthesis

Abstract

In this work, N-Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C–H/N–N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol has been established for the synthesis of isoquinolines using microwave strategy. Use of non-volatile and biodegradable PEG as a green solvent with lower catalyst loading makes the proposed protocol environmentally benign. Further, higher functional group tolerance and wide substrate scope has been observed under the stated methodology with higher yields.

Supporting Information

 
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