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

被引：11
作者：
Vaskevych, Alla I. [1 ]
Savinchuk, Nataliia O. [1 ]
Vaskevych, Ruslan I. [1 ]
Rusanov, Eduard B. [1 ]
Grygorenko, Oleksandr O. [2 ,3 ]
Vovk, Mykhailo V. [1 ]
机构：
[1] Natl Acad Sci Ukraine, Inst Organ Chem, Murmanska Str 5, UA-02660 Kiev, Ukraine
[2] Enamine Ltd, Chervonotkatska Str 78, UA-02094 Kiev, Ukraine
[3] Taras Shevchenko Natl Univ Kyiv, UA-01601 Kiev, Ukraine
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 17卷
关键词：
bis(trifluoroacetoxy)iodo]benzene PIFA; nitrogen heterocycles; oxidative cyclization; pyrrolo[1; 2-a]quinazolines; CYCLOFUNCTIONALIZATION TOTAL-SYNTHESIS; BIOLOGICALLY-ACTIVE QUINOLINE; N-ACYLNITRENIUM IONS; FORMAL SYNTHESIS; DERIVATIVES; IODINE; CONSTRUCTION; ACCESS; QUINAZOLINONES; HYDROAMINATION;
D O I：
10.3762/bjoc.17.189
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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(3H)-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.
引用
收藏
页码：2787 / 2794
页数：8
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