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A new bridgehead nitrogen hetero- cycle viz. 11-carboethoxy-9-oxo-pyrimido[3′2′:3,4]-1,2,4-triazino[5,6-b]indole 3 has been synthesized from 3-azido-5H-1,2,4-triazino[5,6-b]indole 2 by its reaction with diethyl fumerate. The intermediate 2 was obtained by treating 3-hydrazino-5H-1,2,4-triazino[5,6-b]indole with NaNO2 in presence of polyphosphoric acid. A plausible mechanism for the formation of 3 has been formulated and discussed. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:272–276, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20199

The reaction of 1H‐indol‐2,3‐diones with 1,6‐dibromohexane has resulted in the formation of new 1H‐indol‐2,3‐diones‐1,1′‐(1,6‐hexanediyl)bis in quantitative yields. These compounds have been used for the synthesis of novel [3′‐(2,3‐dimethyl‐5‐oxo‐1‐phenyl‐3‐pyrazolin‐4‐yl)spiro[3H‐indol‐3,2′‐thiazolidine]‐2,4′‐dione]‐1,1′‐(1,6‐hexanediyl)bis via bis Schiff's bases, [3‐(2,3‐dimethyl‐5‐oxo‐1‐phenyl‐3‐pyrazolin‐4‐yl) imino‐1H‐indol‐2‐one]‐1,1′‐(1,6‐hexanediyl)bis.