CONDENSED SULFUR-CONTAINING PYRIDINE SYSTEMS. 3. CONSTRUCTION OF PENTA- AND HEXACYCLIC HETEROCYCLIC SYSTEMS BY THE CASCADE REACTION OF 3-CYANOPYRIDINE-2(1<i>H</i>)-THIONES AND 3-CYANOPYRIDINE-2(1<i>H</i>)-THIOLATES WITH 8-CHLOROMETHYL-3-METHYL-7-(2-OXO-2-PHENYLETHYL)XANTHENE
DOI:
https://doi.org/10.1007/963Keywords:
8-chloromethyl-3-methyl-7-(2-oxo-2-phenylethyl)xanthene, 3-cyanopyridine-2(1H)-thiones, thieno[2, 3-b]pyridines, alkylation, cascade reaction, Thorpe-Ziegler reactionAbstract
The alkylation of 3-cyanopyridine-2(1H)-thiones with 8-chloromethyl-3-methyl-7-(2-oxo-2-phenylethyl)- xanthene in a KOH–H2O–DMF system upon heating leads to the formation of pyrido-[3",2":4',5']thieno[3',2':5,6][1,4]diazepino[7,1-f]purine-2,4(3H,6H)-dione derivatives in good yields. Under milder conditions, the intermediates of the cascade reactions, namely, 2-({[3-methyl-2,6-dioxo-7-(2-oxo-2-phenylethyl)-2,3,6,7-tetrahydro-1H-purin-8-yl]methyl}thio)pyridine-3-carbonitriles, can be isolated and characterized.
Authors: V. V. Dotsenko, D. V. Sventukh, and S. G. Krivokolysko
English Translation in Chemistry of Heterocyclic Compounds, 2012, 48 (9), pp 1397-1409
http://link.springer.com/article/10.1007/s10593-012-1149-1