Synthesis and reactions of 1,2,3-triazinium salts

Synthesis

Volumn , Issue 3, 2003, Pages 413-425

  Mättner, Michael ^a   Neunhoeffer, Hans ^a  

^a DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

1,2,3 triazines; Cations; Nucleophilic additions; Regioselectivity; deficient heterocycles

Indexed keywords

SALTS; SYNTHESIS (CHEMICAL);

RING CONTRACTION;

ORGANIC COMPOUNDS;

1,2,3 TRIAZINE DERIVATIVE; CHLOROFORMIC ACID ETHYL ESTER; FLUOROPHOSPHATE; METHYL IODIDE; PERIODATE; PYRAZOLE; SULFONIC ACID DERIVATIVE;

AB INITIO CALCULATION; AMINATION; AQUEOUS SOLUTION; AROMATIZATION; ARTICLE; NUCLEAR OVERHAUSER EFFECT; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; SUBSTITUTION REACTION; SYNTHESIS; TEMPERATURE; THIN LAYER CHROMATOGRAPHY;

EID: 0037233584     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37344     Document Type: Article

References (30)

1. (a) Chupakhin, O. N.; Charushin, V. N.; van der Plas, H. C. In Nucleophilic Aromatic Substitution of Hydrogen; Academic Press: San Diego, 1994,; and references cited therein.
2. (b) Chupakhin, O. N.; Charushin, V. N.; van der Plas, H. C. Tetrahedron 1988, 44, 1.
3. Charushin, V. N.; Chupakhin, O. N.; Sidorov, E. O.; Beiles, Y. I. Zh. Org. Khim. 1978, 14, 140.
4. (a) Rusinov, V. L.; Zyryanov, G. V.; Pilicheva, T. L.; Chupakhin, O. N.; Neunhoeffer, H. J. Heterocycl. Chem. 1997, 34, 1013.
5. (b) Kojevnikov, D. N.; Ulomsky, E. N.; Rusinov, V. L.; Chupakhin, O. N.; Neunhoeffer, H. Mendeleev Commun. 1997, 116.
6. (c) Chupakhin, O. N.; Rusinov, V. L.; Ulomsky, E. N.; Kojevnikov, D. N.; Neunhoeffer, H. Mendeleev Commun. 1997, 66.
7. Stupnikova, T. V.; Petrenko, V. V. Khim. Geterotskil. Soedin. 1984, 1383.
8. Pozharskii, A. F.; Gulevskaya, A. V. Chem. Heterocycl. Cmpds. 2001, 37, 1480; and references cited therein.
9. For a review on 1,2,3-triazines see: (a) Ohsawa, A.; Itoh, T. In Comprehensive Heterocyclic Chemistry II; Boulton, A. J., Ed.; Elsevier: Oxford, 1996, 483-505. (b) Ohsawa, A.; Itoh, T. In Comprehensive Heterocyclic Chemistry II; Boulton, A. J., Ed.; Elsevier: Oxford, 1996, 1177-1307.
10. For a review on 1,2,3-triazines see: (a) Ohsawa, A.; Itoh, T. In Comprehensive Heterocyclic Chemistry II; Boulton, A. J., Ed.; Elsevier: Oxford, 1996, 483-505. (b) Ohsawa, A.; Itoh, T. In Comprehensive Heterocyclic Chemistry II; Boulton, A. J., Ed.; Elsevier: Oxford, 1996, 1177-1307.
11. (a) Okatani, T.; Koyama, J.; Tagahara, K. Heterocycles 1989, 29(9), 1809.
12. (b) Neunhoeffer, H.; Bopp, R.; Diehl, W. Liebigs Ann. Chem. 1993, 367.
13. Neunhoeffer, H.; Clausen, M.; Vötter, H.-D.; Ohl, H.; Krüger, C.; Angermund, K. Liebigs Ann. Chem. 1985, 9, 1732.
14. Ohsawa, A.; Arai, H.; Ohnishi, H.; Kaihoh, T.; Itoh, T.; Yamaguchi, K.; Igeta, H.; Iitaka, Y. Yakugaku Zasshi 1985, 105, 1122.
15. Ohsawa, A.; Itoh, T.; Hasegawa, H.; Nagata, K.; Okada, M. J. Chem. Soc., Perkin. Trans. I 1996, 20, 2511.
16. Meerwein, H. Angew. Chem. 1970, 72, 927.
17. 13
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, J. R.; Cheeseman, J. R.; Keith, T.; Peterson, G. A.; Montgomery, J. A.; Ragharachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. J.; Chen, W.; Wang, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 Rev. D. 4; Gaussian Inc.: Pittsburgh PA, 1995.
19. (a) Pople, J. A.; Schlegel, H. B.; Krishnan, R.; DeFrees, D.; Binkley, J. S.; Frisch, M. J.; Whiteside, R. F.; Hout, R. F.; Hehre, W. J. Int. J. Quantum Chem. Quantum Chem. Symp 1981, 15, 269.
20. (b) Foresman, J. B.; Frisch, M. J. In Exploring Chemistry with Electronic Structures Methods: A Guide to Using Gaussian; Gaussian Inc.: Pittsburgh, 1993.
21. -1
22. Varvoglis, A. In The Organic Chemistry of Polycoordinated Iodine; VCH Publishers Inc.: New York, 1992.
23. (a) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431.
24. (b) Varvoglis, A. Synthesis 1984, 709.
25. (c) Jacobsen, S. A.; Rodbotten, S.; Benneche, T. J. Chem. Soc., Perkin Trans. 1 1999, 22, 3265.
26. Kang, S.-K.; Lee, S.-H.; Lee, D. Synlett 2000, 1022.
27. Neßlers reagent for ammonium salts from Merck VWR International Inc. Darmstadt, see: Burns, E. A.; Streuli, C. A.; Averell, P. R. In The Analytical Chemistry, of Nitrogen and its Compounds; Wiley-Intersience: New York, 1970.
28. (a) Itoh, T.; Okada, M.; Nagata, K.; Yamaguchi, K.; Ohsawa, A. Chem. Pharm. Bull. 1990, 38, 2108.
29. (b) Itoh, T.; Nagata, K.; Kaihoh, T.; Okada, M.; Kawabata, C.; Arai, H.; Ohnishi, H.; Yamaguchi, K.; Igeta, H.; Ohsawa, A.; Iitaka, Y. Heterocycles 1992, 33, 631.
30. Ohsawa, A.; Itoh, T.; Nagata, K.; Okada, M. Chem. Pharm. Bull. 1992, 40, 2283.