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

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(...

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Autores principales: Vaskevych, Alla I, Savinchuk, Nataliia O, Vaskevych, Ruslan I, Rusanov, Eduard B, Grygorenko, Oleksandr O, Vovk, Mykhailo V
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8630437/
https://www.ncbi.nlm.nih.gov/pubmed/34900009
http://dx.doi.org/10.3762/bjoc.17.189
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author Vaskevych, Alla I
Savinchuk, Nataliia O
Vaskevych, Ruslan I
Rusanov, Eduard B
Grygorenko, Oleksandr O
Vovk, Mykhailo V
author_facet Vaskevych, Alla I
Savinchuk, Nataliia O
Vaskevych, Ruslan I
Rusanov, Eduard B
Grygorenko, Oleksandr O
Vovk, Mykhailo V
author_sort Vaskevych, Alla I
collection PubMed
description 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.
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spelling pubmed-86304372021-12-09 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 Vaskevych, Alla I Savinchuk, Nataliia O Vaskevych, Ruslan I Rusanov, Eduard B Grygorenko, Oleksandr O Vovk, Mykhailo V Beilstein J Org Chem Letter 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. Beilstein-Institut 2021-11-25 /pmc/articles/PMC8630437/ /pubmed/34900009 http://dx.doi.org/10.3762/bjoc.17.189 Text en Copyright © 2021, Vaskevych et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Letter
Vaskevych, Alla I
Savinchuk, Nataliia O
Vaskevych, Ruslan I
Rusanov, Eduard B
Grygorenko, Oleksandr O
Vovk, Mykhailo V
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
title 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
title_full 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
title_fullStr 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
title_full_unstemmed 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
title_short 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
title_sort 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
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8630437/
https://www.ncbi.nlm.nih.gov/pubmed/34900009
http://dx.doi.org/10.3762/bjoc.17.189
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