Cyclizations of Alkenyl(Alkynyl)-Functionalized Quinazolinones and their Heteroanalogues: a Powerful Strategy for the Construction of Polyheterocyclic Structures

Chem Rec. 2023 Oct 13:e202300255. doi: 10.1002/tcr.202300255. Online ahead of print.ABSTRACTQuinazolin-4-one, its heteroanalogues, and derivatives represent an outstandingly important class of compounds in modern organic, medicinal, and pharmaceutical chemistry, as these molecular structures are noted for their wide synthetic and pharmacological potential. In the last years, ever-increasing research attention has been paid to quinazolinone derivatives bearing alkenyl and alkynyl substituents on the pyrimidinone nucleus. The original structural combination of synthetically powerful endocyclic amidine (or amidine-related) and exocyclic unsaturated moieties provides a driving force for cyclizations, which offer an efficient toolkit to construct a variety of fused pyrimidine systems with saturated N- and N,S-heterocycles. In this connection, the present review article is mainly aimed at systematic coverage of the progress in using alkenyl(alkynyl)quinazolinones and their heteroanalogues as convenient bifunctional substrates for regioselective annulation of small- and medium-sized heterocyclic nuclei. Much attention is paid to elucidating the structural and electronic effects of reagents on the regio- and stereoselectivity of the cyclizations as well as to clarifying the relevant reaction mechanisms.PMID:37830463 | DOI:10.1002/tcr.202300255

Source: Chemical Record - October 13, 2023 Category: Chemistry Authors: Alla Vaskevych Maryna Dekhtyar Mykhailo Vovk Source Type: research