Ring-chain tautomerism in 2-substituted 1,2,3,4-tetrahydroquinazolines A 1H, 13C and 15N NMR study

Tetrahedron

Volumn 59, Issue 11, 2003, Pages 1939-1950

  Sinkkonen, Jari ^a   Zelenin, Kirill N ^b   Potapov, Abdul Kadir A ^b   Lagoda, Igor V ^b   Alekseyev, Valeriy V ^b   Pihlaja, Kalevi ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b S M KIROV MILITARY MEDICAL ACADEMY   (Russian Federation)

Author keywords

1,2,3,4 tetrahydroquinazolines; Hammett's equation; NMR spectroscopy; Ring chain tautomerism

Indexed keywords

1 (1,2,3,4 TETRAHYDROQUINAZOLIN 2 YL)NAPHTHALEN 2 OL; 2 (1,2,3,4 TETRAHYDROQUINAZOLIN 2 YL)PHENOL; 2 (2 CHLORO 6 NITROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (2 METHOXY 5 NITROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (2,4 DICHLOROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (3 IODOPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (3 NITROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (3,4 DIMETHOXYPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (4 CHLOROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (4 ETHOXYPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (4 FLUOROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (4 METHOXYPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (4 METHOXYPHENYL) 2 METHYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 (4 NITROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 ISOPROPYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 METHYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 METHYL 2 (4 METHYLPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 METHYL 2 (4 NITROPHENYL) 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 METHYL 2 NAPHTHALEN 2 YL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 METHYL 2 PHENYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 METHYL 3,4 DIHYDROQUINAZOLINE; 2 PHENYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2 PROPYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2,2 DIMETHYL 1,2,3,4 TETRAHYDROQUINAZOLINE; 2,4 DICHLORO 6 (1,2,3,4 TETRAHYDROQUINAZOLIN 2 YL)PHENOL; 3',4' DIHYDRO 1'H SPIRO[CYCLOHEXANE 1,2' QUINAZOLINE]; 4 (1,2,3,4 TETRAHYDROQUINAZOLIN 2 YL)PHENOL; N (2 AMINOBENZYL) N [[(4 DIMETHYLAMINO)PHENYL]METHYLENE]AMINE; TETRAHYDROQUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; EQUILIBRIUM CONSTANT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0037430690     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00148-0     Document Type: Article

References (26)

1. (a) Valters R.E., Fülöp F., Korbonits D. Adv. Heterocycl. Chem. 66:1996;1-71
2. (b) Zelenin K.N., Alekseyev V.V., Pihlaja K., Ovcharenko V.V. Russ. Chem. Bull. Int. Ed. 51:2002;1-17.
3. Zelenin K.N., Ukraintsev I.V. Org. Prep. Proced. Int. 30:1998;109-114.
4. Zelenin K.N., Alekseyev V.V., Ukraintsev I.V., Tselinsky I.V. Org. Prep. Proced. Int. 30:1998;53-61.
5. McDonagh A.F., Smith H.E. J. Org. Chem. 33:1968;1-8.
6. McDonagh A.F., Smith H.E. J. Org. Chem. 33:1968;8-12.
7. Alva Astudillo M.E., Chokotho N.C.J., Jarvis T.C., Johnson C.D., Lewis C.C., McDonnell P.D. Tetrahedron. 41:1985;5919-5928.
8. Fülöp F., Pihlaja K., Mattinen J., Bernáth G. J. Org. Chem. 52:1987;3821-3825.
9. Fülöp F., Dahlqvist M., Pihlaja K. Acta. Chem. Scand. 45:1991;273-275.
10. Fülöp F., Forró E., Bernáth G., Miskolczi I., Martinsen A., Vainiotalo P. J. Heterocycl. Chem. 34:1997;289-293.
11. Kempter G., Ziegner H.-J., Moser G., Natho W. Wiss. Z. Pädagog. Hochsch. Karl Liebknecht Potsdam. 21:1977;5-18.
12. Kempter G., Ehrlichmann W., Plesse M., Lehm H.-U. J. Prakt. Chem. 324:1982;832-840.
13. Gravier D., Dupin J.-P., Casadebaig F., Hou G., Petraud M., Moulines J., Barde B. J. Heterocycl. Chem. 28:1991;391-395.
14. Vanden Eynde J.J., Godin J., Mayence A., Maquestiau A., Anders E. Synthesis. 9:1993;867-869.
15. Lessel. J. Arch. Pharm. (Weinheim). 327:1994;329-336.
16. Göblyös A., Lázár L., Fülöp F. Tetrahedron. 58:2002;1011-1016.
17. Lázár L., Göblyös A., Martinek T.A., Fülöp F. J. Org. Chem. 67:2002;4734-4741.
18. Westerman P.W., Botto R.E., Roberts J.D. J. Org. Chem. 43:1978;2590-2596.
19. Zelenin K.N., Lagoda I.V., Alekseyev V.V., Sinkkonen J., Shaikhutdinov R.A., Pihlaja K. J. Heterocycl. Chem. 39:2002;805-810.
20. Neuvonen K., Fülöp F., Neuvonen H., Koch A., Kleinpeter E., Pihlaja K. J. Org. Chem. 66:2001;4132-4140.
21. Zhuo J.-C. Magn. Reson. Chem. 37:1999;259-268.
22. Dziembowska T., Rozwadowski Z., Filarowski A., Hansen P.E. Magn. Reson. Chem. 39:2001;S67-S80.
23. Schilf W., Kamienski B., Dziembowska T. J. Mol. Struct. 602-603:2002;41-47.
24. Braun S., Kalinowski H.-O., Berger S. 150 and More Basic NMR Experiments: A Practical Course. 1998;Wiley-VCH, Weinheim.
25. Ried W., Stahlhofen P. Chem. Ber. 87:1954;1814-1824.
26. Smith J.G., Sheepy J.M. J. Heterocycl. Chem. 12:1975;231-234.