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Gas-phase pyrolysis in organic synthesis: A route for synthesis of cyanamides

✍ Scribed by Nouria A. Al-Awadi; Mervat Mohammed Abdelkhalik; Osman M. E. El-Dusouqui; Mohammad H. Elnagdi

Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
69 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

magnified image

Pyrolysis of 1,7‐di‐[(E)‐1‐morpholinomethylidene]‐ and 1,7‐di‐[(E)‐1‐piperidino‐methylidene]‐4,6,10,12‐tetramethylamino‐2,8‐dioxo‐1,7‐diaza‐3,5,9,11‐cyclododecatetraene‐3,9‐dicarbonitrile 6a, 6b afforded pyridone 10 in addition to cyanamides 11a, 11b. On the other hand, pyrolysis of 1‐[E‐(4‐(__E‐__3‐cyano‐4,6‐dimethyl‐2‐oxopyridin‐1(2H)‐ylimino) methylpiperazin‐1‐yl] methylenamino‐4,6‐dimethyl‐2‐oxo‐1,2‐dihydropyridine‐3‐carbonitrile 8 gave 1‐amino‐4,6‐dimethyl‐2‐oxo‐1,2‐dihydropyridine‐3‐carbonitrile 13 as well as piperazine. The mechanism of pyrolysis and the effect of stereochemistry of pyrolyzed substrates on the nature of the pyrolysates are discussed. J. Heterocyclic Chem., (2010).

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