Dehydration in Water: A Reagentless and Straightforward Synthesis of Tetrahydroquinazolines under Microwave Irradiation or by Stirring at Room Temperature, and Their Subsequent Conversion into Quinazolines in a Micellar Medium

This article is dedicated to Prof. H. Ila, JNCASR, Bangalore on the occasion of her 80^th birthday

Abstract

Using a reagent- and catalyst-free approach, a series of 2-substituted 1,2,3,4-tetrahydroquinazolines is synthesized by cyclocondensation between aldehydes and 2-aminobenzylamines via dehydration in water. The reactions are complete in 2 minutes under microwave irradiation and proceed well under stirring at room temperature, affording tetrahydroquinazolines in high to excellent yields. The products are water-insoluble and are isolated by simple filtration, avoiding a conventional work-up step and offering an organic-solvent-free process. Furthermore, the tetrahydroquinazolines are efficiently oxidized in a micellar medium derived from cetyltrimethylammonium bromide (CTAB) using a cheap commercial bleaching solution (4% NaOCl in water) to give quinazolines in high yields. This sustainable protocol has a near zero E-factor.

Key words

dehydration in water - tetrahydroquinazolines - 2-substituted quinazolines - reagentless - micellar medium

Publication History

Received: 13 May 2024

Accepted after revision: 19 June 2024

Accepted Manuscript online:
19 June 2024

Article published online:
15 July 2024

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