Reactions of quinolizine- and pyridino[1,2-a]pyrimidine-3-diazonium tetrafluoroborates with aliphatic amines

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 59, Issue 4, 2004, Pages 380-385

  Rečnik, Simon ^a   Svete, Jurij ^a   Stanovnik, Branko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Diazonium Salts; Pyridines; Pyrimidines; Rearrangement; Triazenes

Indexed keywords

ALIPHATIC COMPOUNDS; PYRIDINE; SALTS;

ALIPHATIC AMINES; ALIPHATIC PRIMARY AMINES; DIAZONIUM SALTS; PYRIMIDINES; REARRANGEMENT; SECONDARY AMINES; TETRAFLUOROBORATES; TRIAZENES;

AMINES;

1 CYANO 3 (3,3 DICYCLOHEXYLTRIAZ 1 ENYL) 4H QUINOLIZIN 4 ONE; 1 CYANO 3 (3,3 DIETHYLTRIAZ 1 ENYL) 4H QUINOLIZIN 4 ONE; 1 CYANO 3 (PIPERIDIN 1 YLDIAZENYL) 4H QUINOLIZIN 4 ONE; 1 CYANO 3 (PYRROLIDIN 1 YLDIAZENYL) 4H QUINALIZIN 4 ONE; 1 CYANO 4 OXO 4H QUINOLIZINE 3 DIAZONIUM TETRAFLUOROBORATE; 3 (3,3 DIETHYLTRIAZ 1 ENYL) 4H PYRIDINO[1,2 A]PYRIMIDIN 4 ONE; 3 (PIPERIDIN 1 YLDIAZENYL) 4H PYRIDINO[1,2 A]PYRIMIDIN 4 ONE; 3 (PYRROLIDIN 1 YLDIAZENYL) 4H PYRIDINO[1,2 A]PYRIMIDIN 4 ONE; 4 OXO 4H PYRIDINO[1,2 A]PYRIMIDINE 3 DIAZONIUM TETRAFLUOROBORATE; ALIPHATIC AMINE; AMIDE; BORINIC ACID DERIVATIVE; DIAZONIUM COMPOUND; N BUTYLPYRIDINE 2 CARBOXAMIDE; N PENTYLPYRIDINE 2 CARBOXAMIDE; N PROPYLPYRIDINE 2 CARBOXAMIDE; PICOLINIC ACID DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLIZINE DERIVATIVE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 2442536712     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2004-0405     Document Type: Conference Paper

References (29)

1. For a review see: a) H. Zollinger, Diazo Chemistry I: Aromatic and Heteroaromatic Compounds, VCH, Weinheim (1994); b) H. Zollinger, Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds, VCH, Weinheim (1995); D. B. Kimball, M. M. Haley, Angew. Chem. 114, 3484 (2002).
2. For a review see: a) H. Zollinger, Diazo Chemistry I: Aromatic and Heteroaromatic Compounds, VCH, Weinheim (1994); b) H. Zollinger, Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds, VCH, Weinheim (1995); D. B. Kimball, M. M. Haley, Angew. Chem. 114, 3484 (2002).
3. For a review see: a) H. Zollinger, Diazo Chemistry I: Aromatic and Heteroaromatic Compounds, VCH, Weinheim (1994); b) H. Zollinger, Diazo Chemistry II: Aliphatic, Inorganic and Organometallic Compounds, VCH, Weinheim (1995); D. B. Kimball, M. M. Haley, Angew. Chem. 114, 3484 (2002).
4. a) A. Reiser, H.-Y. Shih, T.-F. Yeh, J.-P. Huang, Angew. Chem. Int. Ed. 35, 2428 (1996);
5. b) E. Reichmanis, L. F. Thompson, Chem. Rev. 89, 1273 (1989).
6. a) J. L. Bahr, J. Yang, D. V. Kosynkin, M. J. Bronikowski, R. E. Smalley, J. M. Tour, J. Am. Chem. Soc. 123, 6536 (2001);
7. b) J. L. Bahr, J. M. Tour, Chem. Mater. 13, 3823 (2001);
8. c) J. K. Kariuki, M. T. McDermott, Langmuir 17, 5947 (2001);
9. A. Adenier, M. C. Bernard, M. M. Chehimi, E. Cabet-Deliry, B. Desbat, O. Fagebaume, J. Pinson, F. Povorica, J. Am. Chem. Soc. 123, 4541 (2001).
10. a) M. L. Gross, D. H. Blank, W. M. Welch, J. Org. Chem. 58, 2104 (1993);
11. b) R. Lazny, J. Poplawski, J. Köbberling, D. Enders, S. Bräse, Synlett 1304 (1999);
12. c) R. Lazny, M. Sienkiewicz, S. Bräse, Tetrahedron 57, 5825 (2001).
13. a) S. Bräse, J. Köbberling, D. Enders, R. Lazny, M. Wang, S. Brandtner, Tetrahedron Lett. 40, 2105 (1999);
14. b) V. Krchňák, M. W. Holladay, Chem. Rev. 102, 61 (2002);
15. c) S. Bräse, S. Dahmen, in K. C. Nicolaou, R. Hanko, W. Hartwig (eds): Linkers for Solid-phase Synthesis in Handbook of Combinatorial Chemistry. Drugs, Catalysts, Materials, Vol. 1, p. 59-169, VCH, Weinheim (2002);
16. nd edition, p. 1-504, VCH, Weinheim (2002).
17. a) E. Carvalho, A. P. Francisco, J. Iley, E. Rosa, Bioorg. Med. Chem. 8, 1719 (2000);
18. b) K. Vaughan, Org. Prep. Proced. Int. 33, 59 (2001).
19. For recent reviews see: a) B. Stanovnik, J. Heterocycl. Chem. 36, 1581 (1999); b) B. Stanovnik, J. Svete, Synlett 1077 (2000); c) B. Stanovnik, J. Svete, Targets in Heterocyclic Systems 4, 105 (2000); d) J. Svete, J. Heterocycl. Chem. 39, 437 (2002); e) J. Svete, Monatsh. Chem., in press; f) B. Stanovnik, J. Svete, Chem. Rev. 104 (2004), in press.
20. For recent reviews see: a) B. Stanovnik, J. Heterocycl. Chem. 36, 1581 (1999); b) B. Stanovnik, J. Svete, Synlett 1077 (2000); c) B. Stanovnik, J. Svete, Targets in Heterocyclic Systems 4, 105 (2000); d) J. Svete, J. Heterocycl. Chem. 39, 437 (2002); e) J. Svete, Monatsh. Chem., in press; f) B. Stanovnik, J. Svete, Chem. Rev. 104 (2004), in press.
21. For recent reviews see: a) B. Stanovnik, J. Heterocycl. Chem. 36, 1581 (1999); b) B. Stanovnik, J. Svete, Synlett 1077 (2000); c) B. Stanovnik, J. Svete, Targets in Heterocyclic Systems 4, 105 (2000); d) J. Svete, J. Heterocycl. Chem. 39, 437 (2002); e) J. Svete, Monatsh. Chem., in press; f) B. Stanovnik, J. Svete, Chem. Rev. 104 (2004), in press.
22. For recent reviews see: a) B. Stanovnik, J. Heterocycl. Chem. 36, 1581 (1999); b) B. Stanovnik, J. Svete, Synlett 1077 (2000); c) B. Stanovnik, J. Svete, Targets in Heterocyclic Systems 4, 105 (2000); d) J. Svete, J. Heterocycl. Chem. 39, 437 (2002); e) J. Svete, Monatsh. Chem., in press; f) B. Stanovnik, J. Svete, Chem. Rev. 104 (2004), in press.
23. For recent reviews see: a) B. Stanovnik, J. Heterocycl. Chem. 36, 1581 (1999); b) B. Stanovnik, J. Svete, Synlett 1077 (2000); c) B. Stanovnik, J. Svete, Targets in Heterocyclic Systems 4, 105 (2000); d) J. Svete, J. Heterocycl. Chem. 39, 437 (2002); e) J. Svete, Monatsh. Chem., in press; f) B. Stanovnik, J. Svete, Chem. Rev. 104 (2004), in press.
24. For recent reviews see: a) B. Stanovnik, J. Heterocycl. Chem. 36, 1581 (1999); b) B. Stanovnik, J. Svete, Synlett 1077 (2000); c) B. Stanovnik, J. Svete, Targets in Heterocyclic Systems 4, 105 (2000); d) J. Svete, J. Heterocycl. Chem. 39, 437 (2002); e) J. Svete, Monatsh. Chem., in press; f) B. Stanovnik, J. Svete, Chem. Rev. 104 (2004), in press.
25. S. Rečnik, J. Svete, B. Stanovnik, Eur. J. Org. Chem. 3705 (2001).
26. S. Rečnik, J. Svete, A. Meden, B. Stanovnik, Heterocycles 53, 1793 (2000).
27. T. Kočar, S. Rečnik, J. Svete, B. Stanovnik, ARKIVOC 2002 (part viii), 143 (2002).
28. S. Rečnik, J. Svete, B. Stanovnik, Heterocycles 57, 2091 (2002).
29. J. H. Billman, J. L. Rendall, J. Am. Chem. Soc. 66, 540 (1944).