Synthesis and structure elucidation of pyrimidobenzimidazoles and fused derivatives II [1]. Dodecahydrobenzimidazo-[2,1-b]quinazolines and decahydrobenzimidazo-[2,1-b]benzo[h]quinazolines [2]

Monatshefte fur Chemie

Volumn 131, Issue 4, 2000, Pages 353-374

  Wendelin, Winfried ^a   Gößnitzer, Edith ^a   El Ella, Dalal Abou ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Benzimidazo 2,1 b benzo h quinazolines, trans 8a decahydro; Benzimidazo 2,1 b quinazolines, trans 6a dodecahydro; Conformational analysis; Cyclizations, regiospecific; NMR Spectroscopy

Indexed keywords

EID: 0000927742     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007060050317     Document Type: Article

References (37)

1. For part I, see Abou El Ella D, Gößnitzer E, Wendelin W (1996) J Heterocyclic Chem 33: 373
2. Presented in part at the Fifteenth International Congress of Heterocyclic Chemistry, Taipei, Taiwan (1995) Abstract book, PO3-305
3. Wendelin W, Schermanz K, Kerbl J (1983) Monatsh Chem 114: 717
4. Wendelin W, Kerbl J (1984) Montash Chem 115: 309
5. Wendelin W, Schermanz K (1984) J Heterocyclic Chem 21: 65
6. Wendelin W, Schramm HW, Blasi-Rabassa A (1985) Monatsh Chem 116: 385
7. Wendelin W, Schermanz K, Egger P, Gößnitzer E (1990) Arch Pharm 323: 647
8. Gößnitzer E, Wendelin W, Hocevar-Korosec M, Fellner H (1994) Sci Pharm 62: 178
9. Wendelin W, Schermanz K, Blasi-Rabassa A, Gößnitzer E (1989) Sci Pharm 57: 230
10. Wendelin W et al (unpublished results / in preparation)
11. Abou El Ella D, Gößnitzer E, Wendelin W (1995) Hongkong International Symposium on Heterocyclic Chemistry, Abstract Book. The University of Hongkong, p 108
12. Desenko SM, Orlov VD (1989) Khim Geterotsikl Soedin 8: 1071
13. Desenko SM, Orlov VD, Lipson W, Estrada Kh (1991) Khim Geterotsikl Soedin 9: 1215
14. Bajwa JS, Sykes PS (1979) J Chem Soc Perkin Trans I, 3085
15. Graubaum H, Martin D (1982) J Prakt Chem 324: 569
16. Popov II Boroshko SL, Tertov BA (1989) Khim Geterotsikl Soedin 8: 273
17. Lipson W, Desenko SM, Orlov VD, Ryndina YN, Chuvurin AV, Gorbenko NI, Kirichenko AA (1994) Khim-Farm Zh 28: 14 [Chem Abstr (1995) 123: 246058]
18. Lipson W, Desenko SM, Orlov VD, Ryndina YN, Chuvurin AV, Gorbenko NI, Kirichenko AA (1994) Khim-Farm Zh 28: 14 [Chem Abstr (1995) 123: 246058]
19. Cooper K (Pfizer Ltd, Pfizer Ine) (1990) PCT Int Appl WO 90/10632 [Chem Abstr (1991) 114: 102038]
20. Cooper K (Pfizer Ltd, Pfizer Ine) (1990) PCT Int Appl WO 90/10632 [Chem Abstr (1991) 114: 102038]
21. Lardelli, G, Lamberti V, Weller WT, De Jonge AP (1967) Chem Abstr 67: 32309; Tilichenko MN, Barbulescu E, Barbulescu N (1961) Rec Trav Chim Pays-Bas 12: 631
22. Lardelli, G, Lamberti V, Weller WT, De Jonge AP (1967) Chem Abstr 67: 32309; Tilichenko MN, Barbulescu E, Barbulescu N (1961) Rec Trav Chim Pays-Bas 12: 631
23. Vorländer D, Kunze K (1926) Ber Dtsch Chem Ges 59: 2078; Poggi R, Sacchi S (1940) Gazz chim ital 70: 269
24. Vorländer D, Kunze K (1926) Ber Dtsch Chem Ges 59: 2078; Poggi R, Sacchi S (1940) Gazz chim ital 70: 269
25. Hassner A, Cromwell NH (1957) J Am Chem Soc 79: 230; Cromwell NH, Bamburg RE (1959) J Am Chem Soc 81: 4294
26. Hassner A, Cromwell NH (1957) J Am Chem Soc 79: 230; Cromwell NH, Bamburg RE (1959) J Am Chem Soc 81: 4294
27. Dietrich B, Fyles DL, Lehn JM (1979) HeIv Chim Acta 62: 2763
28. Relative positions are designated by application of the α,β system [25]. Accordingly, the substituent at the chiral center with the lowest locant (H-6a in case of 4C,T, aryl at C-7 in case of 5C,T) is always designated as α and serves as reference point. In order to achieve proper presentations of the formulae and stereo-formulae, α-substituents in Schemes and Figures are drawn, as required, below or above the ring plane. Axially and equatorially directed protons are marked with ax and eq, respectively.
29. All reactions were carried out with racemic trans-3n-20 and yielded mixtures of racemic diastereomers 4C,T and 5C,T, respectively. In order to point out clearly the steric relations of α-and β-arranged substituents, the Schemes and Figures show, as substitutes for racemates, only enantiomers derived from either (3aR,7aR)-20 or (3aS,7aS)-20.
30. International Union of Pure and Applied Chemistry, Commission on Nomenclature of Organic Chemistry (Rigandy J, Klesny SP, 1979), Nomenclature of Organic Chemistry, Section E-4.11 (Extension of the α,β system). Pergamon Press, Oxford, New York, Toronto, Sydney, Paris, Frankfurt, p 482
31. Bax A, Freeman R, (1981) J Magn Reson 44: 542
32. Kay LE, Keifer P, Saarinen T (1992) J Am Chem Soc 114: 10663
33. Wilker W, Leibfritz D, Kerssebaum R, Bermel W (1993) Magn Reson Chem 31: 287
34. Kinns M, Sanders JKM (1984) J Magn Reson 56: 518
35. Kessler H, Oschkinat H, Griesinger, C, Bermel W (1986) J Magn Reson 70: 106
36. Gößnitzer E (1994) PhD Thesis, Karl Franzens University Graz, p 35
37. Abd El Nabi OM, Reisinger EC, Reinthaler FF, Still F, Eibel U, Krejs GJ (1992) J Ethno-pharmacol 37: 77