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Catalytic Intramolecular Cycloaddition Reactions by Using a Discrete Molecular Architecture

Roy, Bijan and Devaraj, Anthonisamy and Saha, Rupak and Jharimune, Suprita and Chi, Ki-Whan and Mukherjee, Partha Sarathi (2017) Catalytic Intramolecular Cycloaddition Reactions by Using a Discrete Molecular Architecture. In: CHEMISTRY-A EUROPEAN JOURNAL, 23 (62). pp. 15704-15712.

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Official URL: http://doi.org/10.1002/chem.201702507

Abstract

A discrete tetragonal tube-shaped complex (MT-1) has been synthesised by coordination-driven self-assembly of a carbazole-based tetraimidazole donor L and a Pd(II) 90 degrees acceptor, that is, cis-(dppf)Pd(OTf)(2)] (dppf=diphenylphosphinoferrocene, OTf=CF3SO3-). Complex MT-1 was characterised by multinuclear NMR, ESI-MS and single-crystal X-ray diffraction analysis (SCXRD), which showed its symmetrical tetrafacial tube-shaped architecture possessing a large cavity described by four aromatic walls. This coordination cage was successfully utilised as a molecular vessel to perform intramolecular cycloaddition reactions of O-allylated benzylidinebarbituric acid derivatives inside its confined nanospace. The presence of a catalytic amount of MT-1 promoted 4+2] cycloaddition reactions in a regio- and stereoselective manner, yielding the corresponding penta/tetracyclouracil derivatives in good yields under mild reaction conditions. This protocol is interesting compared with the literature reports for the synthesis of similar chromenopyran pyrimidinedione derivatives under high-temperature reflux conditions or solid-state melt reactions (SSMRs).

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the WILEY-V C H VERLAG GMBH, POSTFACH 101161, 69451 WEINHEIM, GERMANY
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 24 Nov 2017 10:15
Last Modified: 24 Nov 2017 10:15
URI: http://eprints.iisc.ac.in/id/eprint/58299

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