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Towards a green synthesis of isoquinoline: Beckmann rearrangement of E,-cinnamaldoxime over H-zeolites

Thomas, Bejoy and Prabhu, Uday R and Prathapan, S and Sugunan, S (2007) Towards a green synthesis of isoquinoline: Beckmann rearrangement of E,-cinnamaldoxime over H-zeolites. In: Microporous and Mesoporous Materials, 102 (1-3). 138 -150.

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Official URL: http://dx.doi.org/10.1016/j.micromeso.2006.12.006

Abstract

Isoquinoline was prepared through the Beckmann rearrangement of cinnamaldoxime over different H-zeolites, K-10 montmorillonite clay, amorphous SiO2–Al2O3 and γ-alumina under well-optimized conditions of temperature, weight hourly space velocity and catalyst loading. Cinnamaldoxime under ambient reaction conditions over the catalysts underwent migration of the anti-styryl moiety to electron deficient nitrogen (Beckmann rearrangement) followed by an intramolecular cyclization to yield isoquinoline. Cinnamo-nitrile (dehydration product) and cinnamaldehyde were formed as by-products. Isoquinoline formation was high on zeolite catalysts (ca. >86.5%) and mordenite (ca. 92.3%) was the most efficient in the series. Catalysts were susceptible for deactivation and the decrease in the percentage conversion of oxime with time is associated with a corresponding increase in the acid hydrolysis producing salicylaldehyde at later stages of the reaction. However, these catalysts retain activity considerably and can be recycled without loss of activity and change of product distribution.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Elsevier Science.
Department/Centre: Division of Chemical Sciences > NMR Research Centre (Formerly SIF)
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 08 Jun 2010 09:18
Last Modified: 02 Nov 2011 08:09
URI: http://eprints.iisc.ernet.in/id/eprint/26903

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