Scaffold Diversity through a Branching Double Annulation Cascade Strategy: An Iminium Induced One-pot Synthesis of Diverse Fused Tetrahydroisoquinoline (THIQ) Scaffolds

D S, Sharada and Shinde, A H and MaliPatel, Srilaxmi and Shinde, V (2016) Scaffold Diversity through a Branching Double Annulation Cascade Strategy: An Iminium Induced One-pot Synthesis of Diverse Fused Tetrahydroisoquinoline (THIQ) Scaffolds. Journal of Organic Chemistry, 81 (15). pp. 6463-6471. ISSN 0022-3263

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Abstract

A branching double annulation cascade (BDAC) strategy for diverse and complex fused THIQ scaffolds via a highly reactive iminium induced one-pot double cyclization sequence involving Pictect-Spengler type cyclization has been developed for the first time. The salient features of this protocol are direct and rapid access to unprecedented diverse fused THIQ skeletons, metal/catalyst free, cleaner reaction profile, good to excellent yields and convenient approach. This catalyst-free domino process facilitates the double annulation with variety of scaffold building agents via two C-N and one C-X (X = C, N, O) bonds formation in a single step, under uniform reaction conditions. Furthermore, we reveal an unusual dual BDAC sequence leading to N-N linked isoquinoline dimer.

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IITH Creators:
IITH CreatorsORCiD
D S, SharadaUNSPECIFIED
Item Type: Article
Subjects: Chemistry > Organic chemistry
Divisions: Department of Chemistry
Depositing User: Team Library
Date Deposited: 21 Jul 2016 11:55
Last Modified: 01 Apr 2019 09:09
URI: http://raiithold.iith.ac.in/id/eprint/2565
Publisher URL: http://dx.doi.org/10.1021/acs.joc.6b01096
OA policy: http://www.sherpa.ac.uk/romeo/issn/0022-3263/
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