Triazene derivatives of (1,x)-diazacycloalkanes. Part V. Synthesis and characterization of 4-ethyl-3-({6-ethyl-3-[2-aryl-1-diazenyl]hexahydro-1- pyrimidinyl}methyl)-1-[2-aryl-1-diazenyl]hexahydropyrimidines from the reaction of diazonium salts with mixtures of formaldehyde and 1,3-diaminopentane

Canadian Journal of Chemistry

Volumn 83, Issue 10, 2005, Pages 1799-1807

  Tingley, Reid ^a   Peori, M Brad ^a   Church, Ryan ^a   Vaughan, Keith ^a  

^a SAINT MARY S UNIVERSITY   (Canada)

Author keywords

Diaminopentane; Diastereotopic protons; Diazacycloalkanes; Diazonium coupling; Hexahydropyrimidine; Stereocenter; Triazene

Indexed keywords

CARBON; NUCLEAR MAGNETIC RESONANCE; SALTS; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

DIAMINOPENTANE; DIASTEREOTOPIC PROTONS; DIAZACYCLOALKANES; DIAZONIUM COUPLING; HEXAHYDROPYRIMIDINE; STEREOCENTER; TRIAZENE;

AROMATIC HYDROCARBONS;

1,3 DIAMINOPENTANE; 4 ETHYL 3 [[6 ETHYL 3 (1 DIAZENYL)HEXAHYDRO 1 PYRIMIDINYL]METHYL] 1 (1 DIAZENYL)HEXAHYDROPYRIMIDINE DERIVATIVE; BICYCLO COMPOUND; CARBENE; CARBON; CYCLOALKANE; DIAMINE; DIAZONIUM COMPOUND; ETHYLENEDIAMINE; FORMALDEHYDE; FUNCTIONAL GROUP; HETEROCYCLIC COMPOUND; NITROGEN; PENTANE; PROTON; PYRIMIDINE DERIVATIVE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CROSS LINKING; DIASTEREOISOMER; ELEMENTAL ANALYSIS; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; NUCLEAR MAGNETIC RESONANCE; SIGNAL DETECTION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 33644847641     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v05-192     Document Type: Article

References (25)

1. D.B. Kimball and M.M Haley. Angew. Chem. Int. Ed. 41, 3338 (2002);
2. D.B. Kimball, R. Herges, and M.M. Haley. J. Am. Chem. Soc. 124, 1572 (2002).
3. S. Brase. Acc. Chem. Res. 37, 805 (2004).
4. T.A. Connors, P.M. Goddard, K. Merai, W.C.J. Ross, and D.E.V. Wilman. Biochem. Pharmacol. 25, 241 (1976);
5. G. Daidone, D. Raffa, B. Maggio, M.V. Raimondi, F. Plescia, and D. Schillachi. Eur. J. Med. Chem. 39, 219 (2004).
6. E.S. Newlands, G.R.P. Blackledge, J.A. Slack, C. Goddard, C.J. Brindley, L. Holder, and M.F.G. Stevens. Cancer Treat. Rep. 69, 801 (1985).
7. K.C. Nikolau, C.N.C. Boddy, S. Brase, and N. Wissinger. Angew. Chem. Int. Ed. 38, 2097 (1999).
8. D.L. Hooper, I.R. Pottie, M. Vacheresse, and K. Vaughan. Can. J. Chem. 76, 125 (1998).
9. K. Vaughan. Org. Prep. Proced. Int. 33, 59 (2001).
10. S. Moser, R. Church, M.B. Peori, and K. Vaughan. Can. J. Chem. 83, 1071 (2005);
11. M.B. Peori, K. Vaughan, and V. Bertolasi. J. Chem. Crystallogr. 35, 297 (2005).
12. R. Tingley, V. Bertolasi, and K. Vaughan. J. Chem. Crystallogr. 35, 821 (2005).
13. H. Krassig. Makromol. Chem. 17, 77 (1955).
14. R.F. Evans. Aust. J. Chem. 20, 1643 (1967).
15. M.M. Bagga, B. Everett, and I.G. Hinton. Chem. Commun. (Cambridge), 259 (1987).
16. J. Dale and T. Sigvartsen. Acta Chem. Scand. 45, 1064 (1991).
17. M.B. Peori, K. Vaughan, and D.L. Hooper. J. Org. Chem. 63, 7437 (1998).
18. K. Biradha, M.B. Peori, K. Vaughan, and M.J. Zaworotko. J. Chem. Crystallogr. 29, 145 (1999).
19. J.F. Glister, K. Vaughan, and V. Bertolasi. J. Chem. Crystallogr. 34, 175 (2004).
20. V.R. Little and K. Vaughan. Can. J. Chem. 82, 1294 (2004).
21. V.R. Little, R. Tingley, and K. Vaughan. Can. J. Chem. 83, 471 (2005).
22. S.L. Moser and K. Vaughan. Can. J. Chem. 82, 1725 (2004).
23. M. Barra, S. Srivastava, and E. Brockman. J. Phys. Org. Chem. 17, 1057 (2004);
24. B.T. Golding, T.J. Kemp, R. Narayanaswamy, and B.W. Waters. J. Chem. Res. (S), 130 (1984).
25. R.D. Singer, K. Vaughan, and D.L. Hooper. Can. J. Chem. 64, 1567 (1986).