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Synthesis and stereochemistry of indano[1,2-d][1,3]oxazines and thiazines, new ring systems

✍ Scribed by Märta Palkó; Anasztäzia Hetényi; Ferenc Fülöp

Publisher
Journal of Heterocyclic Chemistry
Year
2004
Tongue
English
Weight
236 KB
Volume
41
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A set of structurally varied indano[1,2‐d][1,3]oxazines and thiazines, which are new ring systems, were prepared by ring‐closure reactions of amino alcohols 4–6. The reactions of cis‐ and trans‐1‐amino‐ and cis‐ 1‐benzylamino‐2‐hydroxymethylindane (4–6) with 1 equivalent of an aromatic aldehyde in methanol at room temperature resulted in three‐component equilibria (15a‐g), or a Schiff base (16), or a ring‐closure product alone (17a‐c), respectively, depending on the substitution or configuration of the starting amino alcohol. The ring‐chain tautomeric equilibria can be described by an equation of Hammett type.

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## Abstract magnified image A simple and efficient synthesis of substituted benzo [1,3] oxazine and benzo [1,3] thiazine derivatives under conventional heating, as well as microwave irradiation is reported. The compounds were obtained by the reaction of electron rich phenols, formaldehyde, and aro