Protoberberines from Reissert-Compounds VIII [1]. Oxazoloisoquinolines, New and Efficient Educts for the Synthesis of 8-Oxoprotoberberines

Monatshefte fur Chemie

Volumn 134, Issue 7, 2003, Pages 991-1014

  Reimann, Eberhard ^a   Grasberger, Fritz ^a   Polborn, Kurt ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

13a Carboxy 8 oxo protoberberines; 8 Oxoprotoberberines; Oxazoloisoquinolinones; X ray crystal structure

Indexed keywords

PROTOBERBERINE DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; BENZYLATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; PRECURSOR; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0038796082     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-003-0013-5     Document Type: Article

References (40)

1. VII: Reimann E, Grasberger F, Polborn K (2000) Monatsh Chem 131: 73
2. Matulenko MA, Meyers AJ (1996) J Org Chem 61: 573 and further lit cited therein
3. Zhang JS, le Men-Olivier L, Massiot G (1995) Phytochemistry 39: 439
4. Nimgirawath S, Ponghusabun O (1994) Austr J Chem 47: 951
5. Grigg R, Sridharan V, Stevenson P, Sukhirthalingam S, Worakun T (1990) Tetrahedron 46: 4003
6. Huang WJ, Singh OV, Chen CH, Chion SY, Lee SS (2002) Helv Chim Acta 85: 1069
7. Lou ZC, Gao CY, Lin FT, Zhang J, Lin MC, Sharaf M, Wong LK, Slatkin DJ, Schiff PL Jr (1992) Planta Medica 58: 114
8. Leete E, Murril JB (1967) Phytochemistry 6: 231
9. Reimann E, Benend H (1992) Monatsh Chem 123: 939
10. Gibson HW (1970) J Heterocyclic Chem 7: 1169
11. Cook MJ, Katritzky AR, Page AD (1977) J Am Chem Soc 99: 165
12. Jackson YA, Stephenson EK, Cava M (1993) Heterocycles 36: 1047
13. Cava MP, Noguchi J (1972) J Org Chem 37: 2936
14. Kido K, Watanabe Y (1980) Heterocycles 14: 1151
15. Chantimakorn V, Nimgirawath S (1989) Austr J Chem 42: 209
16. Tilley JW, Danho W, Lovey K, Wagner R, Swistok J, Makofske R, Michalewsky J, Triscari J, Nelson D, Weatherford S (1991) J Med Chem 34: 1125
17. Jones JA (1964) J Org Chem 29: 3531
18. Roclofsen DP, DeGraaf JWM, Hagendoorn JA, Verschoor HM, Van Bekkum H (1970) Recl Trav Chim Pays-Bas 89: 193
19. Hauser FM, Pogany SA (1980) Synthesis, 814
20. Grethe G, Lee HL, Uskokovic M, Brossi A (1968) J Org Chem 33: 494
21. Cushman M, Choong T, Valko JT, Koleck MP (1980) J Org Chem 45: 5067
22. Ziegler FE, Fowler KW (1976) J Org Chem 41: 1564
23. Eliel EL, Ferdinand TN, Carolyn SRM (1954) J Org Chem 19: 1693
24. Dean RT, Rappoport H (1978) J Org Chem 43: 2115
25. Meyers AJ, Gabel R, Mihelich E (1978) J Org Chem 43: 1372
26. Jahangir, Fisher LE, Clark RD, Muchowski JM (1989) J Org Chem 54: 2992
27. Eicher T, Tiefensee K, Pick R (1988) Synthesis, 525
28. Ollero L, Castedo L, Domingez D (1999) Tetrahedron 55: 4445
29. Lutz RE, Bailey PS, Rowlett RJ Jr, Wilson JW, Allison RK, Clark MT, Leake NH, Jordan RH, Keller RJ, Nicodemus KC (1947) J Org Chem 12: 760
30. Wang W, Obeyesekere NU, McMurray JS (1996) Tetrahedron Letters 37: 6661
31. Reimann E, Höglmüller A (1985) Arch Pharm (Weinheim) 318: 487
32. Neumeyer JL, Oh KH, Weinhardt KK, Neustadt BR (1969) J Org Chem 34: 3786
33. Ruchirawat S (1978) Heterocycles 9: 1345
34. Reimann E, Renz H (1993) Arch Pharm (Weinheim) 323: 253
35. Hung TV, Mooney BA, Prager RH (1981) Austr J Chem 34: 151
36. Kessar VS, Singh P, Vohra R, Kaur NP, Venugopal D (1992) J Org Chem 57: 6716
37. Ruchirawat S, Lertwanawatana W, Thepchumrune P (1980) Tetrahedron Letters 21: 189
38. Jahangir, MacLean DB, Holland H (1987) Can J Chem 65: 727
39. Li M, Chen X, Tang QM, Zhang JS (2001) Planta Medica 67: 189
40. Sheldrick GM, Programs for the Solution and Refinement of Crystal Structures, Göttingen, 1990 and 1993