Vaskevych Alla, Dekhtyar Maryna, Vovk Mykhailo
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv 02660, Ukraine.
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Academician Kukhar str., 5, Kyiv, 02660, Ukraine.
Chem Rec. 2024 Feb;24(2):e202300255. doi: 10.1002/tcr.202300255. Epub 2023 Oct 13.
Quinazolin-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.
喹唑啉-4-酮及其杂环类似物和衍生物是现代有机化学、药物化学和制药化学中一类极其重要的化合物，因为这些分子结构以其广泛的合成和药理潜力而闻名。在过去几年中，嘧啶酮核上带有烯基和炔基取代基的喹唑啉酮衍生物受到了越来越多的研究关注。合成能力强大的内环脒（或与脒相关）和外环不饱和部分的原始结构组合为环化提供了驱动力，这为构建各种具有饱和N-和N,S-杂环的稠合嘧啶系统提供了一个有效的工具包。就此而言，本综述文章主要旨在系统地介绍使用烯基（炔基）喹唑啉酮及其杂环类似物作为方便的双功能底物用于中小尺寸杂环核的区域选择性环合的进展。重点关注阐明试剂对环化反应的区域和立体选择性的结构和电子效应，以及阐明相关的反应机理。
