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

A regioselective method for the synthesis of 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2- ]quinazolin-5(1 )-ones - close structural analogs of naturally occurring vasicinone alkaloids - is described. The procedure is based on PIFA-initiated oxidative 5- cyclization of 2-(3-butenyl)quinazolin-4(3 )-ones...

Full description

Saved in:
Bibliographic Details
Published in:Beilstein journal of organic chemistry 2021, Vol.17 (1), p.2787-2794
Main Authors: Vaskevych, Alla I, Savinchuk, Nataliia O, Vaskevych, Ruslan I, Rusanov, Eduard B, Grygorenko, Oleksandr O, Vovk, Mykhailo V
Format: Article
Language:English
Subjects:
[bis(trifluoroacetoxy)iodo]benzene pifa
Chemistry
Letter
nitrogen heterocycles
oxidative cyclization
pyrrolo[1,2-a]quinazolines
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A regioselective method for the synthesis of 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2- ]quinazolin-5(1 )-ones - close structural analogs of naturally occurring vasicinone alkaloids - is described. The procedure is based on PIFA-initiated oxidative 5- cyclization of 2-(3-butenyl)quinazolin-4(3 )-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.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.17.189