The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3 H)-ones - an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2- a]quinazolin-5(1 H)-ones

Alla I Vaskevych; Nataliia O Savinchuk; Ruslan I Vaskevych; Eduard B Rusanov; Oleksandr O Grygorenko; Mykhailo V Vovk

doi:10.3762/bjoc.17.189

The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3 H)-ones - an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2- a]quinazolin-5(1 H)-ones

Beilstein J Org Chem. 2021 Nov 25:17:2787-2794. doi: 10.3762/bjoc.17.189. eCollection 2021.

Authors

Alla I Vaskevych¹, Nataliia O Savinchuk¹, Ruslan I Vaskevych¹, Eduard B Rusanov¹, Oleksandr O Grygorenko^{2

3}, Mykhailo V Vovk¹

Affiliations

¹ Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska str. 5, Kyiv 02660, Ukraine.
² Enamine Ltd, Chervonotkatska str. 78, Kyiv 02094, Ukraine.
³ Taras Shevchenko National University of Kyiv, Kyiv 01601, Ukraine.

Abstract

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.

Keywords: [bis(trifluoroacetoxy)iodo]benzene PIFA; nitrogen heterocycles; oxidative cyclization; pyrrolo[1,2-a]quinazolines.