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

Prashishkumar K. Shirsat; Navnath B. Khomane; Sneha H. Meshram; Balasubramanian Sridhar; Harshadas M. Meshram; Ravindra M. Kumbhare

doi:10.1055/s-0037-1610999

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(06): 1473-1481
DOI: 10.1055/s-0037-1610999

paper

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

Authors

Prashishkumar K. Shirsat

^aAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India

^bMedicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India eMail: hmmeshram@yahoo.com
Navnath B. Khomane

^aAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India

^bMedicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India eMail: hmmeshram@yahoo.com
Sneha H. Meshram

^aAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201002, India

^bMedicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India eMail: hmmeshram@yahoo.com
Balasubramanian Sridhar

^cCentre for X-ray Crystallography, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India
Harshadas M. Meshram*

^bMedicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India eMail: hmmeshram@yahoo.com
Ravindra M. Kumbhare*

^dFluoroorganic Division, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad 500007, India eMail: kumbhare@iict.res.in

Abstract

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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.

Key words

ninhydrin - anilines - 3,4-dihydroisoquinolin-2(1H)-ones - methanolysis - tandem cyclization

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