Selective synthesis of octahydroacridines and diannelated pyridines over zinc-containing mesoporous aluminosilicate molecular sieve catalysts?

Dalton Transactions Pub Date: 2019-08-09 DOI: 10.1039/C9DT01196J

Abstract

We demonstrate a very eco-friendly and single-step catalytic method for the highly selective synthesis of 1,2,3,4,5,6,7,8-octahydroacridine (OHA) by the vapour phase aminocyclization of cyclohexanone (Cy[double bond, length as m-dash]O) with a mixture of formaldehyde (HCHO) and ammonia (NH3) over mesoporous bimetallic ZnAlMCM-41 (ZnAl-41) molecular sieves as efficient catalysts, which were synthesised by a simple basic hydrothermal method. To find optimum parameters for the synthesis of OHA, different reaction parameters, such as temperature, time on stream (TOS), weight hourly space velocity (WHSV), and feed molar ratios of Cy[double bond, length as m-dash]O?:?HCHO?:?NH3, have been extensively studied. The used ZnAl-41 catalysts were treated by washing and calcination to recover the recyclable catalysts which were then reused in these reactions to study their catalytic abilities. To selectively synthesize a variety of pyridine compounds, the active mesoporous catalysts, namely, ZnAl-41(75) and recyclable ZnAl-41(75), with different reaction parameters, were extensively used in the vapour phase aminocyclization reaction with different aldehydes and cycloketones, and produced excellent product selectivities, e.g., 9-alkyl substituted octahydroacridines (9-ASOHAs) and diannelated pyridines (DAPs), with good ketone conversions. In this catalytic reaction, OHA, 9-ASOHAs and DAPs are the main products and are important as starting materials in the preparation of biologically active compounds, drugs, dyes and alkaloids. It is shown by our remarkable catalytic results that the ZnAl-41(75) catalyst, as an environmentally friendly heterogeneous catalyst, has outstanding catalytic activity in the production of OHA, 9-ASOHAs and DAPs by a single-step synthetic method.

Graphical abstract: Selective synthesis of octahydroacridines and diannelated pyridines over zinc-containing mesoporous aluminosilicate molecular sieve catalysts
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