Bisiminopropadienes R-N=C=C=C=N-R from Pyridopyrimidines
Heidi Gade Andersen A B , David Kvaskoff A and Curt Wentrup A C
+ Author Affiliations
- Author Affiliations
A School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, Qld 4072, Australia.
B Current address: Cheminova A/S, 7620 Lemvig, Denmark.
C Corresponding author. Email: wentrup@uq.edu.au
Australian Journal of Chemistry 65(6) 686-689 https://doi.org/10.1071/CH12039
Submitted: 24 January 2012 Accepted: 10 May 2012 Published: 1 June 2012
Abstract
Chlorination of the N,N′-di(2-pyridyl)malonamide 13a affords 2-chloro-8-methyl-4-(2-(4-picolinyl)imino-4H-pyrido[1,2-a]pyrimidine 17a. Flash vacuum thermolysis of 17a causes efficient ring opening to the valence-tautomeric ketenimine 18a/19a, elimination of HCl, and formation of the bis(4-methyl-2-pyridyl)iminopropadiene, R-N=C=C=C=N-R 20a.
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