Issue 12, 2016
From the journal:

Chemical Communications

Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones†

Subramani Rajkumar,a   S. Antony Savarimuthu,b   Rajendran Senthil Kumaran,c   C. M. Nagarajad  and  Thirumanavelan Gandhi*a  

* Corresponding authors

a Materials Chemistry Division, School of Advanced Sciences, VIT University, Tamil Nadu 632014, India
E-mail: velan.g@vit.ac.in

b Department of Chemistry, St. Xavier's College, Palayamkottai, Tamil Nadu 627002, India

c Syngene International Limited, Biocon, Bangalore, India

d Department of Chemistry, Indian Institute of Technology Ropar, Punjab 140001, India

Abstract

Ruthenium-catalyzed simple, cascade and one-pot synthesis of cinnoline-fused diones has been carried out by the C–H activation of phthalazinones/pyridazinones accomplished by the unusual deoxygenation of propargyl alcohols. The bond selectivity is accredited to the traceless directing nature of the hydroxyl group of propargyl alcohol. A sequential C–H activation, insertion and deoxy-oxidative annulation has been proposed based on the preliminary mechanistic study.

Graphical abstract: Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

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Article information

DOI
https://doi.org/10.1039/C5CC09347C
Article type
Communication
Submitted
11 Nov 2015
Accepted
14 Dec 2015
First published
14 Dec 2015

Chem. Commun., 2016,52, 2509-2512

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Expedient synthesis of new cinnoline diones by Ru-catalyzed regioselective unexpected deoxygenation-oxidative annulation of propargyl alcohols with phthalazinones and pyridazinones

S. Rajkumar, S. Antony Savarimuthu, R. Senthil Kumaran, C. M. Nagaraja and T. Gandhi, Chem. Commun., 2016, 52, 2509 DOI: 10.1039/C5CC09347C

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