TY - JOUR A1 - Vaskevych, Alla I. A1 - Savinchuk, Nataliia O. A1 - Vaskevych, Ruslan I. A1 - Rusanov, Eduard B. A1 - Grygorenko, Oleksandr O. A1 - Vovk, Mykhailo V. T1 - The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3H)-ones – an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones JF - Beilstein Journal of Organic Chemistry PY - 2021/// VL - 17 SP - 2787 EP - 2794 SN - 1860-5397 DO - 10.3762/bjoc.17.189 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.17.189 KW - [bis(trifluoroacetoxy)iodo]benzene PIFA KW - nitrogen heterocycles KW - oxidative cyclization KW - pyrrolo[1,2-a]quinazolines N2 - A regioselective method for the synthesis of 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-ones – close structural analogs of naturally occurring vasicinone alkaloids – is described. The procedure is based on PIFA-initiated oxidative 5-exo-trig cyclization of 2-(3-butenyl)quinazolin-4(3Н)-ones, in turn prepared by thermal cyclocondensation of the corresponding 2-(pent-4-enamido)benzamides. The products obtained have a good natural product likeness (NPL) score and therefore can be useful for the design of natural product-like compound libraries. ER -