Journal
TETRAHEDRON
Volume 68, Issue 2, Pages 488-498Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.11.018
Keywords
Alkynes; Enediynes; Anionic cyclizations; Quinoxalines; Pteridines; Pyrido[2,3-b]pyrazines
Categories
Funding
- Russian Foundation for Basic Research [11-03-00079-a]
Ask authors/readers for more resources
The reactivity of 3-alkynyl-2-chloroquinoxalines, 2,3-dialkynylquinoxalines, and some related pyrazine derivatives toward carbanions of the CH-acids (malononitrile, ethyl cyanoacetate, diethyl malonate, 1,3-dimethylbarbituric acid) has been studied. Most of the observed reactions proceeded as tandem or cascade cyclizations yielding polynuclear heterocyclic compounds. The process starts with the addition of a nucleophile to an alkyne triple bond. Depending on the nature of the used C-nucleophile, the thus formed anionic adduct underwent further cyclization via (i) intramolecular nucleophilic substitution of the chlorine atom, (ii) intramolecular acylation of the ring nitrogen atom by the ester side chain or (iii) intramolecular nucleophilic attack on the second C C bond. Reactions of 3-alkyny1-2-chloro- and 2,3-dialkynylpyrazines with 1,3-dimethylbarbituric acid in the presence of t-BuOK were accompanied by recyclization of the 1,3-dimethylbarbituric acid moiety. (C) 2011 Elsevier Ltd. All rights reserved.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available