Intramolecular azide-alkene cycloaddition-elimination reaction in an aldohex-2-enonic acid derivative

Add time:08/24/2019    Source:sciencedirect.com

A 6-azido-2-tosylenolate, obtained from D-glucono-1,5-lactone in six steps, underwent an intramolecular cycloaddition–elimination pathway under mild conditions, yielding a chiral, substituted 5,6-dihydro-4H-pyrrolo[1,2-c]-1,2,3-triazole. The conditions were optimized to give exclusive formation of the triazole. The mechanism appears to involve intramolecular ring closure via a 1,3-dipolar azide–alkene cycloaddition to give a 1,2,3-triazoline, followed by elimination of p-toluenesulfonic acid, leading to aromatization. Triazole products, obtained by chemical modification, are expected to display activity as enzyme inhibitors. Furthermore, partially protected derivatives of the 2-hexenoate were prepared as useful synthetic intermediates.

We also recommend Trading Suppliers and Manufacturers of 3-Methyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid (cas 17245-60-2). Pls Click Website Link as below: cas 17245-60-2 suppliers

Prev:Claisen rearrangements—III : Convenient syntheses of the coumarins, osthenol, demethylsuberosin and Coumurrayin (cas 17245-25-9)☆
Next:Chemical characterization of cytotoxic indole acetic acid derivative from mulberry fruit (Morus alba L.) against human cervical cancer)