Synthesis of 2-oxo-2,3,5,6-tetrahydro-5-thioxoimidazo[1,2-c]quinazolines by one-pot cyclization of α-aminocarboxylic esters with 2-(isothiocyanato)benzonitrile (ITCB)

Tetrahedron

Volumn 62, Issue 33, 2006, Pages 7653-7660

  Bodtke, Anja ^a   Reinke, Helmut ^b   Michalik, Dirk ^c   Langer, Peter ^b,c  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

^c LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Amino acids; Cyclizations; Domino reactions; Isothiocyanates; Regioselectivity

Indexed keywords

2 (4 ISOPROPYL 2,5 DIOXOIMIDAZOLIDIN 1 YL)BENZONITRILE; 2 (4,4 DIMETHYL 5 OXO 2 THIOXOIMIDAZOLIDIN 1 YL)BENZONITRILE; 2 (ISOTHIOCYANATO)BENZONITRILE; 2 OXO 2,3,5,6 TETRAHYDRO 5 THIOXOIMIDAZO[1,2 C]QUINAZOLINE; 3 (2 CYANOPHENYL) 2 THIOXO 1,3 DIAZASPIRO[4,5]DECAN 4 ONE; 3 (2 CYCLOHEXYLETHYL) 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 (2 HYDROXYETHYL) 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 BENZYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 ETHYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 ISOBUTYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 ISOPROPYL 2,5 DIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLINE; 3 ISOPROPYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 METHYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3 PHENYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 3,3 DIMETHYL 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; 4 METHYL 6 THIOXO3,4,5,6 TETRAHYDROPYRIMIDINO[2,3 C]QUINAZOLIN 2 ONE; 5 THIOXO 5,6 DIHYDROIMIDAZO[1,2 C]QUINAZOLIN 2 ONE; BENZONITRILE; BENZYL (2 OXO 5 THIOXO 2,3,5,6 TETRAHYDROIMIDAZO[1,2 C]QUINAZOLIN 3 YL)ACETATE; ESTER DERIVATIVE; ETHYL 2 OXO 5 THIOXO 2,3,5,6 TETRAHYDROIMIDAZO[1,2 C]QUINAZOLIN 3 CARBOXYLATE; QUINAZOLINE DERIVATIVE; SPIROCYCLOHEXAN 1,3' (2 OXO 2 THIOXO 4,5 DIHYDROIMIDAZO[1,2 C]QUINAZOLINE); UNCLASSIFIED DRUG;

ARTICLE; ATOM; CONCENTRATION (PARAMETERS); CYCLIZATION; MELTING POINT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIZATION; REACTION ANALYSIS; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION;

EID: 33745620141     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.05.075     Document Type: Article

References (26)

1. Besson T., Guillard J., Rees C.W., and Thiéry V. J. Chem. Soc., Perkin Trans. 1 (1998) 889
2. Leardini R., Nanni D., Pareschi P., Tundo A., and Zanardi G. J. Org. Chem. 62 (1997) 8394
3. Calestani G., Capella L., Leardini R., Minozzi M., Nanni D., Papa R., Romina R., and Zanardi G. Tetrahedron 57 (2001) 7221
4. Pavia M.R., Lobbestael S.J., Taylor C.P., Hershenson F.M., and Miskell D.L. J. Med. Chem. 33 (1990) 854
5. Pfeiffer W.-D., Hetzheim A., Pazdera P., Bodtke A., and Mücke J. J. Heterocycl. Chem. 36 (1999) 1327
6. Francis J.E., Cash W.D., Barbaz W.D., Bernard P.S., Lovell R.A., Mazzenga G.C., Friedmann R.C., Hyun J.L., Braunwalder A.F., Loo P.S., and Bennett D.A. J. Med. Chem. 34 (1991) 281
7. Francis J.E., Cash W.D., Psychoyos S., Ghai G., Wenk P., Friedmann R.C., Atkins C., Warren V., Furness P., Hyun J.L., Stone G.A., Desai M., and Williams M. J. Med. Chem. 31 (1988) 1014
8. Blank J., Kandt M., Pfeiffer W.-D., Hetzheim A., and Langer P. Eur. J. Org. Chem. (2003) 182
9. Langer P., and Bodtke A. Tetrahedron Lett. (2003) 5965
10. Albrecht U., and Langer P. Synlett (2004) 1963
11. Bodtke A., and Langer P. Tetrahedron Lett. 45 (2004) 8741
12. Pfeiffer W.D., Pazdera P., Hetzheim A., and Muecke J. Pharmazie 50 (1995) 21
13. Langer P., and Bodtke A. Synlett (2003) 1743
14. Cianci C., Chung T.D.Y., Menwell N., Putz H., Hagen M., Colonno R.J., and Krystal M. Antiviral Chem. Chemother. 7 (1996) 353
15. Gineinah M.M., Ismaiel A.M., and El-Kerdawy M.M. J. Heterocycl. Chem. 27 (1990) 723
16. Liu K.C., and Hu M.K. Arch. Pharm. (Weinheim, Ger.) 319 (1986) 188
17. Kottke, K.; Kuehmstedt, H.; Graefe, I.; Wehlau, H.; Knocke, D. DD 253,623, 1988;
18. Chem. Abstr. 109 (1988) 17046
19. Kathawala, F.; Hardtmann, G. E. Ger. Offen. 2,146,076, 1972;
20. Chem. Abstr. 77 (1972) 48501
21. Kathawala, F.; Hardtmann, G. E. Ger. Offen. 2,261,095, 1971;
22. Chem. Abstr. 79 (1973) 66385
23. Chowdhury A.Z.M.S., Shibata Y., Morita M., Kaya K., and Sano T. Heterocycles 55 (2001) 1747
24. Papadopoulos E.P. J. Heterocycl. Chem. 18 (1981) 515
25. Kottke K., Kühnstedt K., and Griesner G. Pharmazie 38 (1983) 367
26. Crystallographic data (excluding structure factors) for the structure in this paper (6a) have been deposited in the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-603359. Copies of these data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk or via www.ccdc.cam.ac.uk/conts/retrieving.html.