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.
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| http://dx.doi.org/10.3762/bjoc.17.189 | DOI Listing |
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The PIFA-initiated oxidative cyclization of 2-(3-butenyl)quinazolin-4(3)-ones - an efficient approach to 1-(hydroxymethyl)-2,3-dihydropyrrolo[1,2-]quinazolin-5(1)-ones.
Beilstein J Org Chem
November 2021
Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska str. 5, Kyiv 02660, Ukraine.
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.
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