Facile acid-catalyzed condensation of 2-hydroxy-2,2′-biindan-1, 1′,3,3′-tetrone with phenols, methoxyaromatic systems and enols

Tetrahedron

Volumn 60, Issue 45, 2004, Pages 10197-10205

  Das, Suven ^a   Pramanik, Animesh ^a   Fröhlich, Roland ^b   Patra, Amarendra ^a  

^a UNIVERSITY OF CALCUTTA   (India)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

2 Hydroxy 2,2 biindan 1,1 ,3,3 tetrone; Chromenes; Electrophilic addition; Enols; Phenols

Indexed keywords

1 NAPHTHOL; 2 (1 HYDROXYNAPHTHYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (2 HYDROXYNAPHTHYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (2 METHYL 4 HYDROXY 5 ISOPROPYLPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (2,4 DIHYDROXY 3 ACETYLPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (2,4 DIHYDROXY 6 METHYLPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (2,4 DIHYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (2,4,6 TRIHYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (3 CHLORO 4 HYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (3 METHOXY 4 HYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (3 METHYL 4 HYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (3,4 DIHYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 (4 HYDROXYPHENYL) 2,2' BIINDAN 1,1',3,3' TETRONE; 2 HYDROXY 2,2' BIINDAN 1,1',3,3' TETRONE; 2 NAPHTHOL; 6 BROMO 2',4 SPIRO(1',3' INDANEDION)INDENO[3,2 B]CHROMENE; 6 CHLORO 2',4 SPIRO(1',3' INDANEDION)INDENO[3,2 B]CHROMENE; 6 METHOXY 2',4 SPIRO(1',3' INDANEDION)INDENO[3,2 B]CHROMENE; 6 METHYL 2',4 SPIRO(1',3' INDANEDION)INDENO[3,2 B]CHROMENE; 7 METHYL 2',4 SPIRO(1',3' INDANEDION)INDENO[3,2 B]CHROMENE; ACETAL; ACID; AROMATIC COMPOUND; CHROMENE DERIVATIVE; COUMARIN DERIVATIVE; INDAN DERIVATIVE; PHENOL; PHLOROGLUCINOL; RESORCINOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; MOLECULE; POLYMERIZATION; PRIORITY JOURNAL; X RAY DIFFRACTION;

EID: 4644328682     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.004     Document Type: Article

References (32)

1. S. Ruhemann Trans. Chem. Soc. 97 1910 1438
2. D.A. MacFadyen, and N. Fowler J. Biol. Chem. 186 1950 13
3. M.M. Joullié, and T.R. Thompson Tetrahedron 47 1991 8791
4. T.D. Schertz, R.C. Reiter, and C.D. Stevenson J. Org. Chem. 66 2001 7596
5. Das, S.; Pramanik, A. Unpublished work.
6. F. Campagna, A. Carotti, G. Casini, and M. Ferappi Gazz. Chim. Ital. 113 1983 507
7. A. Schoenberg, and E. Singer Chem. Ber. 103 1970 3871
8. N.P. Peet, E.W. Huber, and J.C. Huffman J. Heterocycl. Chem. 32 1995 33
9. D.St.C. Black, M.C. Bowyer, G.C. Condie, D.C. Craig, and N. Kumar Tetrahedron 50 1994 10983
10. S.K. Kundu, A. Pramanik, and A. Patra Synlett 5 2002 823
11. J.L. Bullington, and J.H. Dodd J. Org. Chem. 58 1993 4833
12. J.N. Usmani, and S.M. Ismail Pak. J. Sci. Ind. Res. 30 1987 89
13. S.K. Kundu, A. Patra, and A. Pramanik Indian J. Chem. 43B 2004 604
14. J.-P. Poupelin, G. Saint-Ruf, J.-C. Perche, B. Laude, G. Narcisse, F. Bakri-Logesis, and F. Hubert Eur. J. Med. Chem. 15 1980 253
15. J.-P. Poupelin, G. Saint-Ruf, J.-C. Perche, R. Lacroix, G. Uchida-Ernouf, G. Narcisse, and F. Hubert Eur. J. Med. Chem. 14 1979 171
16. G. Schmitt, A.N. Dinh, J.-P. Poupelin, J. Vebrel, and B. Laude Synthesis 1984 758
17. T. Yamazaki, and T. Takizawa Tetrahedron 28 1972 4675
18. H.N. Song, M.R. Seong, J.S. Son, and J.N. Kim Synth. Commun. 28 1998 1865
19. D.A. Klumpp, S. Fredrick, S. Lau, K.K. Jin, R. Bau, G.K. Surya Prakash, and G.A. Olah J. Org. Chem. 64 1999 5152
20. L.A. Campbell, B.J. Morrison, and O.C. Musgrave J. Chem. Res. (S) 2002 638
21. Olah, G. A. In Friedel-Crafts and Related Reactions, Wiley: New York, 1964; Vol. 2, pp 597-640.
22. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
23. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
24. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
25. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
26. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
27. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
28. Data set were collected with a Nonius KappaCCD diffractometer, equipped with a rotating anode generator Nonius FR591. Programs used: data collection COLLECT (Nonius B.V., 1998), data reduction Denzo-SMN (Otwinowski, Z.; Minor, W. Methods in Enzymology 1997, 276, 307-326), absorption correction data SORTAV (Blessing, R. H. Acta Crystallogr. 1995, A51, 33-37; Blessing, R. H. J. Appl. Cryst. 1997, 30, 421-426), structure solution SHELXS-97 (Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473), structure refinement SHELXL-97 (Sheldrick, G. M. Universität Göttingen, 1997), graphics SCHAKAL (Keller, E. 1997). Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication CCDC-240992, 240993, 233350, 240994, and 240995. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: int. code +44-1223-336-033, e-mail: deposit@ccdc.cam.ac.uk ].
29. Green, G. R.; Evans, J. M.; Vong, A. K. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Seriven, E. F. V., Eds.; Pergamon: New York, 1996; Vol. 5, pp 469-500.
30. G. Vanags, and G. Duburs Zhurnal Obshchei Khimii 27 1957 2729
31. A.D. Panashchenko Farmakol. i Toksikol 19 1956 17
32. G. Vanags, S. Giller, L. Geita, Z.D. Bleksmit, V.N. Kovalenko, and M.A. Kotovshchikova Farmakol. i Toksikol 19 1956 23