Synthetic approach to spiropyranocoumarins and their oxime derivatives

Author:

Krasylov Igor V.1ORCID,Moskvina Viktoriia2ORCID,Khilya Volodymyr P.1ORCID

Affiliation:

1. Taras Shevchenko National University of Kyiv, Kyiv, Ukraine

2. Taras Shevchenko National University of Kyiv, Kyiv, Ukraine; V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the NAS of Ukraine, Kyiv, Ukraine

Abstract

This study explores the synthesis of a diverse series of linear (spiro)pyranocoumarins and their corresponding oximes, compounds known for their promising biological activities. Building on previous work, the authors expand the array of target compounds, adding structural features such as dimethyl groups and various cycloaliphatic rings. The novel synthetic procedure applied herein couples o-hydroxyacetyl coumarins with respective ketones via Kabbe condensation, yielding 16 derivatives, including 12 new compounds. A further step engages these (spiro)pyranocoumarins with hydroxylamine hydrochloride, leading to oximes, selectively at the exocyclic oxygen atom of the chroman-4-one fragment. Optimizing synthesis conditions has increased product yields and reduced reaction times. Acidic hydrolysis of select compounds introduces additional carbonyl groups and facilitates deprotection, while the subsequent reaction with hydroxylamine hydrochloride produces dual-oxime compounds. These findings contribute to the ongoing development of pyranocoumarin and oxime-based therapeutics, with potential applications in treating various diseases

Funder

Ministry of Education and Science of Ukraine

Publisher

National Academy of Sciences of Ukraine (Co. LTD Ukrinformnauka) (Publications)

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