ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Substituted coumarins as ambident nucleophiles in one-pot hydrogenation/alkylation reaction

Nevena I. Petkova-Yankova and Rositca D. Nikolova

Department of Organic Chemistry and Pharmacognosy, Faculty of Chemistry and Pharmacy, Sofia University “St. Kliment Ohridski”, Sofia, Bulgaria

E-mail: nipetkova@chem.uni-sofia.bg

Received: 30 August 2019  Accepted: 10 February 2020

Abstract:

The regioselectivity of a one-pot hydrogenation/alkylation reaction of coumarins 1a and 1b with series of alkyl halides has been elucidated as a complementary work to reaction of acylation with the same coumarins. Reaction conditions have provided formation of only C-alkylation products with good to high yield. The results from the experiments are of significant importance to predict reactivity of 3-substituted coumarins in different reaction conditions.

Keywords: Coumarins; Phosphonates; C-alkylation; Alkylation reaction; Tandem reactions

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-020-01098-1

Chemical Papers 74 (8) 2627–2634 (2020)