An efficient synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones via a CuI-catalyzed deacylation and no dehydration reaction

A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3 H )-one was disclosed in DMF catalyzed by CuI/ l -proline in the presence of Cs 2 CO 3 . This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synt...

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Bibliographic Details
Published in:Monatshefte für Chemie 2019-07, Vol.150 (7), p.1305-1315
Main Authors: Miao, Wei-Qing, Liu, Jian-Quan, Wang, Xiang-Shan
Format: Article
Language:English
Subjects:
Analytical Chemistry
Carbonyls
Chemical reactions
Chemical synthesis
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Dehydration
Diketones
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Proline
Theoretical and Computational Chemistry
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Summary:A novel and efficient annulation of pentane-2,4-dione with 2-(2-bromophenyl)quinazolin-4(3 H )-one was disclosed in DMF catalyzed by CuI/ l -proline in the presence of Cs 2 CO 3 . This procedure experienced the consecutive α-arylation of carbonyl, deacylation but no dehydration reaction for the synthesis of 6-hydroxy-6-methyl-5,6-dihydro-8 H -isoquinolino[1,2- b ]quinazolin-8-ones in good yields. Graphical abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-019-02430-6