Azole additions upon azinium salts

Tetrahedron

Volumn 53, Issue 40, 1997, Pages 13959-13968

  Lavilla, Rodolfo ^a   Gotsens, Teresa ^a   Guerrero, Marta ^a   Masdeu, Carme ^a   Santano, M Carmen ^a   Minguillón, Cristina ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030991653     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00906-X     Document Type: Article

References (27)

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3. c) Sausins, A.; Duburs, G. Heterocycles, 1988, 27, 291-314;
4. d) Comins, D.; O'Connor, S. Adv. Heterocycl. Chem. 1988, 44, 199-267.
5. Lavilla, R.; Gotsens, T.; Bosch, J. Synthesis 1991, 842-844.
6. Lavilla, R.; Gotsens, T.; Guerrero, M.; Bosch, J. Synthesis 1995, 382-384.
7. Lavilla, R.; Gotsens, T.; Gavaldà, J.; Santano, M.C.; Bosch, J. J. Chem. Res. (S) 1996, 380-381.
8. Goldmann, S.; Stoltefuss, J. Angew. Chem. Int. Ed. Engl. 1991, 30, 1559-1578.
9. For the use of chiral auxiliaries in the asymmetric synthesis of dihydropyridines, see: a) Amman, R.; Spitzner, D. Angew. Chem. Int. Ed. Engl. 1991, 30, 1320-1321;
10. b) Mangeney, P.; Gosmini, R.; Raussou, S.; Commerçon, M.; Alexakis, A. J. Org. Chem. 1994, 59, 1877-1888;
11. c) Génisson, Y.; Marazano, C.; Das, B.C. J. Org. Chem. 1993, 58, 2052-2057;
12. d) Amat, M.; Coll, M.D. ; Bosch, J. Tetrahedron 1995, 51, 10759-10770.
13. Minguillón, C.; Franco, P.; Oliveros, L.; López, P. J. Chromatogr., A. 1996, 728, 407-414.
14. s=2.10. Similar values were obtained for the other compounds of this series.
15. O'Donnel, M.J., "Asymmetric Phase-Transfer Reactions", in Catalytic Asymmetric Synthesis; Ojima, I. , Ed.; VCH: New York, 1993; pp. 389-411.
16. O'Donnell, M.J.; Wu, S.; Huffman, J.C. Tetrahedron 1994, 50, 4507-4518.
17. The use of other organic solvents or other catalysts resulted in practically no e.e.
18. For a similar process, see: Alvarez, M.; Lavilla, R.; Bosch, J. Heterocycles 1989, 29, 237-242.
19. Literature refers only to the detection of the 1,2-isomer: von Dobeneck, H.; Goltzsche, W. Chem. Ber. 1969, 95, 1484-1492.
20. For recent and alternative way to control the regioselectivity of the additions to quinolinium salts, see: Grignon-Dubois, M.; Diaba, F.; Grellier-Marly, M.-C. Synthesis, 1994, 800-804.
21. For the isolation of 2-pyridones in this type of reactions, see: Lavilla, R.; Gotsens, T.; Rodríguez, S.; Bosch, J. Tetrahedron 1992, 48, 6445-6454.
22. For instance, only two examples of imidazole addition to N-alkylpyridinium salts have been disclosed very recently: Winter, J.; Rétey, J. Chem. Eur. J. 1997, 3, 410-416.
23. +, 24); 217 (100); 210 (29).
24. Bergman, J.; Goonewardena,H. Acta Chem. Scan., Ser.B, 1980, 34, 763-766.
25. 1H-NMR 2.33 (bs, 6H, CH3); 4.34 (bs, 2H, H-4 pyr); 5.20 (bs, 2H, H-5 pyr); 6.02 (s, 2H, H-3 and H-4 pyrrole); 6.70, 7.20 and 7.60 (3 bs, 4H, H-2 and H-6 pyr); 8.45 (bs, 1H, NH).
26. Compounds 15 and 16 have been reported in the literature without rigurous proof of their structure: Sheinkman, A. K.; Deikalo, A. A. Khim. Getreotsikl. Soedin. 1971, 7, 1654-1659.
27. See, for instance: Brewster, M.E.; Simay, A.; Czako, K.; Winwood, D.; Farag, H.; Bodor, N. J. Org. Chem. 1989, 54, 3721-3726.