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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 11, pp 1445–1454 | Cite as

Condensed isoquinolines 25. Alkylation of 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one

  • L. M. Potikha
  • V. A. KovtunenkoEmail author
Article

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.

Keywords

3,9-dioxo-3H,9H,11H-benzo[5,6][1,8]naphthyridino[1,8-ab]quinazoline-2-carbonitrile isoquino[3,2-b]quinazoline spiro[6,11-dihydro-13H-isoquino[3,2-b]quinazoline-6,2′-indan]-13-one alkylation 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  1. 1.Taras Shevchenko National UniversityKievUkraine

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