Synthesis 2019; 51(06): 1473-1481
DOI: 10.1055/s-0037-1610999
paper
© Georg Thieme Verlag Stuttgart · New York

Base-Catalyzed Tandem Cyclization: Diastereoselective Access to the 3,4-Dihydroisoquinolin-2(1H)-one Core

Prashishkumar K. Shirsat
a  Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India
b  Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India   Email: hmmeshram@yahoo.com
,
Navnath B. Khomane
a  Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India
b  Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India   Email: hmmeshram@yahoo.com
,
Sneha H. Meshram
a  Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India
b  Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India   Email: hmmeshram@yahoo.com
,
Balasubramanian Sridhar
c  Centre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India
,
Harshadas M. Meshram*
b  Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India   Email: hmmeshram@yahoo.com
,
Ravindra M. Kumbhare*
d  Fluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India   Email: kumbhare@iict.res.in
› Author Affiliations
The authors thank CSIR, New Delhi for financial support as part of the XII five-year plan program under the title ACT ().
Further Information

Publication History

Received: 01 August 2018

Accepted after revision: 05 September 2018

Publication Date:
14 November 2018 (eFirst)

Abstract

A novel, one-pot reaction for the synthesis of 3,4-dihydroisoquinolin-2(1H)-one derivatives is developed via a base-mediated three-component reaction of ninhydrin, aniline and acetylenic esters. This diastereoselective reaction takes place in methanol at 70 °C under transition-metal-free conditions, and direct construction of the C–N and C–C bonds is readily achieved via tandem cyclization. These cyclic frameworks are resourceful small molecular keys to many natural products.

Supporting Information

 
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