BF3 center dot OEt2 mediated metal-free one-pot sequential multiple annulation cascade (SMAC) synthesis of complex and diverse tetrahydroisoquinoline fused hybrid molecules

Shinde, A H and Shinde, V and D S, Sharada (2016) BF3 center dot OEt2 mediated metal-free one-pot sequential multiple annulation cascade (SMAC) synthesis of complex and diverse tetrahydroisoquinoline fused hybrid molecules. Organic and Biomolecular Chemistry, 14 (12). pp. 3207-3211. ISSN 1477-0520

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Abstract

A highly efficient and distinct BF3 center dot OEt2 mediated metal-free SMAC protocol for the synthesis of complex and diverse hybrid molecules viz. indazole fused tetrahydroisoquinolinoquinoxalines, and tetrahydroisoquinolinodiazepine has been developed. The transformation is based on sequential cascade processes involving 2H-indazole formation and deprotection Pictet-Spengler cyclization steps in one-pot fashion. The protocol demonstrates the utility of sequential multiple annulations in a cascade fashion. The present one-pot protocol uses the Solid State Melt Reaction (SSMR) strategy for the synthesis of the intermediate 2H-indazole. The method is operationally simple and represents a new approach for C-C, three C-N and N-N bond formation with a wide substrate scope.

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IITH Creators:

IITH Creators	ORCiD
D S, Sharada	UNSPECIFIED

Item Type:

Article

Uncontrolled Keywords:

C,N-Cyclic Azomethine Imines; State Melt Reaction; 1,3-Dipolar Cycloaddition; Substituted Indazoles; Asymmetric-Synthesis; Aerobic Conditions; Branching Cascade; Mild Conditions; 2h-Indazoles; Scaffolds

Subjects:

Chemistry > Organic chemistry
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Divisions:

Department of Chemistry

Depositing User:

Team Library

Date Deposited:

11 Apr 2016 05:49

Last Modified:

21 Apr 2016 09:57

URI:

http://raiithold.iith.ac.in/id/eprint/2271