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Gas‐phase pyrolysis in organic synthesis: A route for synthesis of cyanamides
Author(s) -
AlAwadi Nouria A.,
Abdelkhalik Mervat Mohammed,
ElDusouqui Osman M. E.,
Elnagdi Mohammad H.
Publication year - 2010
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.217
Subject(s) - chemistry , pyrolysis , piperazine , organic chemistry , phase (matter) , medicinal chemistry
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).