CONDENSED ISOQUINOLINES. 25. ALKYLATION OF 6,11-DIHYDRO-13H-ISOQUINO[3,2-<i>b</i>]QUINAZOLIN-13-ONE

Abstract

Interaction of 6,11-dihydro-13H-isoquino[2,3-b]quinazolin-13-one with alkylating agents occurs at two positions depending on their nature and the reaction conditions – at C(6) or N(5). Fusion with methyl tosylate leads  to 5-methyl-13-oxo-6,13-dihydro-11H-isoquino[3,2-b]quinazolin-5-ium  salts, while interaction with benzyl halides in the presence of i-PrONa gave  6-benzyl- and 6,6-dibenzyl-6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-ones. Alkylation with olefins led to two types of products. In the case of maleinimides and maleic acid anhydride Michael adducts at C(6)  were formed and in the case of cyanocinnamic acid esters the reaction was accompanied by intramolecular acylation at N(5) to give 1-aryl-3,9-dioxo-3H,9H,11H-benzo[5,6][1,8]naphthyridino[1,8-ab]quinazoline-2-carbonitrile. 

Статья в английском издании журнала: DOI

How to Cite
Potikha, L. M.; Kovtunenko, V. A.  Chem. Heterocycl. Compd. 2007, 43, 1445. [Khim. Geterotsikl. Soedin. 2007, 1698.]

For this article in the English edition see DOI 10.1007/s10593-007-0223-6