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Bisiminopropadienes R-N=C=C=C=N-R from Pyridopyrimidines
Heidi Gade
Andersen
A
B
,
David
Kvaskoff
A
and
Curt
Wentrup
A
C
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 http://dx.doi.org/10.1071/CH12039
Submitted: 24 January 2012 Accepted: 10 May 2012 Published:
1
June
2012
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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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References
[1]
(a) H. Bibas, D. W. J. Moloney, R. Neumann, M. Shtaiwi, P. V. Bernhardt, C. Wentrup, J. Org. Chem. 2002, 67, 2619.
| CrossRef | CAS |  (b) B. E. Fulloon, C. Wentrup, Aust. J. Chem. 2009, 62, 115.
| CrossRef |
[2]
D. Lecoq, B. A. Chalmers, R. N. Veedu, D. Kvaskoff, P. V. Bernhardt, C. Wentrup, Aust. J. Chem. 2009, 62, 1631.
| CrossRef | CAS |
[3]
C. Plüg, W. Frank, C. Wentrup, J. Chem. Soc., Perkin Trans. 2 1999, 1087.
[4]
M. Shtaiwi, C. Wentrup, J. Org. Chem. 2002, 67, 8558.
| CrossRef | CAS |
[5]
H. G. Andersen, C. Wentrup, Aust. J. Chem. 2012, 65, 105.
| CrossRef | CAS |
[6]
D. Kvaskoff, C. Wentrup, Aust. J. Chem. 2010, 63, 1694.
| CrossRef | CAS |
[7]
R. Wolf, S. Stadtmüller, M. W. Wong, M. Barbieux-Flammang, R. Flammang, C. Wentrup, Chem. – Eur. J. 1996, 2, 1318.
| CrossRef | CAS |
[8]
A. E. Tschitschibabin, Ber. Dtsch. Chem. Ges. 1924, 57, 1168.
| CrossRef |
[9]
(a) N. Thorup, O. Simonsen, Acta Crystallogr. C 1985, 41, 472.
| CrossRef | (b) O. Simonsen, Acta Crystallogr. C 1986, 42, 573.
| CrossRef |
[10]
C. Plüg, B. Wallfisch, H. G. Andersen, P. V. Bernhardt, L.-J. Baker, G. R. Clark, M. W. Wong, C. Wentrup, J. Chem. Soc., Perkin Trans. 2 2000, 2096.
| CrossRef |
[11]
P. V. Bernhardt, C. Wentrup, Aust. J. Chem. 2012, 65, 371.
| CAS |
[12]
G. R. Lappin, Q. R. Petersen, C. E. Wheeler, J. Org. Chem. 1950, 15, 377.
| CrossRef | CAS |
[13]
M. Gullu, L. A. Razack, J. H. P. Utley, R. J. King, G. R. White, Tetrahedron 1991, 47, 675.
| CrossRef | CAS |
[14]
G. Roma, M. Di Braccio, A. Balbi, M. Mazzei, A. Ermili, J. Heterocycl. Chem. 1987, 24, 329.
| CrossRef | CAS |
[15]
D. Maillard, A. Schriver, J. P. Perchard, G. Girardet, J. Chem. Phys. 1979, 71, 505.
IR spectrum of HCl in Ar matrix: | CrossRef | CAS |
[16]
H. B. Bürgi, J. D. Dunitz, Acc. Chem. Res. 1983, 16, 153.
| CrossRef |
[17]
H. G. Andersen, U. Mitchke, C. Wentrup, J. Chem. Soc., Perkin Trans. 2 2001, 602.
| CrossRef |
[18]
(a) J. J. Finnerty, C. Wentrup, J. Org. Chem. 2005, 70, 9735.
| CrossRef | CAS | (b) R. Koch, J. J. Finnerty, C. Wentrup, J. Org. Chem. 2011, 76, 6024.
| CrossRef |
[19]
(a) G. G. Qiao, J. Andraos, C. Wentrup, J. Am. Chem. Soc. 1996, 118, 5634.
| CrossRef | CAS | (b) G. Kollenz, S. Holzer, C. O. Kappe, T. S. Delvi, W. M. F. Fabian, H. Sterk, M. W. Wong, C. Wentrup, Eur. J. Org. Chem. 2001, 1315.
[20]
C. Addicott, C. Wentrup, Aust. J. Chem. 2008, 61, 592.
| CrossRef | CAS |
|
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