Synthesis and Stereochemistry of Indano[1,2-d][1,3]oxazines and Thiazines, New Ring Systems

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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.

Original languageEnglish
Pages (from-to)69-75
Number of pages7
JournalJournal of Heterocyclic Chemistry
Volume41
Issue number1
DOIs
Publication statusPublished - jan. 1 2004

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ASJC Scopus subject areas

  • Organic Chemistry

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