Synthesis of arylated highly congested indans using a domino sequence

Tetrahedron

Volumn 63, Issue 41, 2007, Pages 10300-10308

  Pratap, Ramendra ^a   Kumar, Brijesh ^a   Ram, Vishnu Ji ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

2 Oxo 2H pyrans; Indan; Regioselective

Indexed keywords

5 (4 METHYLPIPERIDIN 1 YL) 7 PHENYLINDAN 4 CARBONITRILE; 5 (PIPERIDIN 1 YL) 7 (THIOPHEN 2 YL)INDAN 4 CARBONITRILE; 5 METHYLSULFANYL 7 (PYRIDIN 3 YL)INDAN 4 CARBONITRILE; 5 METHYLSULFANYL 7 (THIOPHEN 2 YL)INDAN 4 CARBONITRILE; 5 METHYLSULFANYL 7 PHENYLINDAN 4 CARBOXYLIC ACID; 5,6 DIARYL 4 METHYLSULFANYL 2 OXO 2H PYRAN 3 CARBONITRILE; 6 ARYL 4 METHYLSULFANYL 2 OXO 2H PYRAN 3 CARBONITRILE; 6 ARYL 4 SEC AMINO 2 OXO 2H PYRAN 3 CARBONITRILE; 6,7 DIARYL 5 METHYLSULFANYLINDAN 4 CARBONITRILE; 7 (2,4 DIMETHYLPHENYL) 5 METHYLSULFANYLINDAN 4 CARBONITRILE; 7 (4 BROMOPHENYL) 5 (PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; 7 (4 BROMOPHENYL) 5 METHYLSULFANYLINDAN 4 CARBOXYLIC ACID METHYL ESTER; 7 (4 CHLOROPHENYL) 5 (PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; 7 (4 CHLOROPHENYL) 5 METHYLSULFANYLINDAN 4 CARBOXYLIC ACID; 7 (4 METHOXYPHENYL) 5(PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; 7 (4 METHYLPHENYL) 5 (PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; 7 (4 METHYLPHENYL) 5 METHYLSULFANYLINDAN 4 CARBONITRILE; 7 (FURAN 2 YL) 5 METHYLSULFANYLINDAN 4 CARBONITRILE; 7 (NAPHTHALEN 2 YL) 5 (PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; 7 ARYL 5 (PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; 7 ARYL 5 METHYLSULFANYLINDAN 4 CARBONITRILE; 7 ARYL 5 METHYLSULFANYLINDAN 4 CARBOXYLIC ACID; 7 ARYL 5 METHYLSULFANYLINDAN 4 CARBOXYLIC ACID METHYL ESTER; 7 PHENYL 5 (PIPERIDIN 1 YL)INDAN 4 CARBONITRILE; INDAN DERIVATIVE; METHYL 5,6 DIARYL 4 METHYLSULFANYL 2 OXO 2H PYRAN 3 CARBOXYLATE; METHYL 6 ARYL 4 METHYLSULFANYL 2 OXO 2H PYRAN 3 CARBOXYLATE; METHYL 6,7 DIARYL 5 METHYLSULFANYLINDAN 4 CARBOXYLATE; METHYL 7 ARYL 5 METHYLSULFANYLINDAN 4 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

AMINATION; ARTICLE; CATALYSIS; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; ELECTRON; HYDROLYSIS; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SUBSTITUTION REACTION;

EID: 34548239229     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.07.050     Document Type: Article

References (51)

1. Capon R.J., MacLeod J.K., and Scammells P.J. Tetrahedron 42 (1986) 6545
2. MacLeod J.K., and Monahan L.C. Aust. J. Chem. 43 (1990) 329
3. Lee M., Ikeda I., Kawabe T., Mori S., and Kanematsu K. J. Org. Chem. 61 (1996) 3406
4. Ho T.-L., Lee K.-Y., and Chen C.-K. J. Org. Chem. 62 (1997) 3365
5. Ly T.-M., Quiclet-Sire B., Sortais B., and Zard S.Z. Tetrahedron Lett. 40 (1999) 2533
6. Hisaindee S., and Clive D.L.J. Tetrahedron Lett. 42 (2001) 2253
7. Degos L. Leuk. Res. 14 (1990) 717
8. Ulmschneider S., Müller-Vieira U., Klein C.D., Antes L., Lengauer T., and Hertmann R.W. J. Med. Chem. 48 (2005) 1563
9. Pass M., Abu-Rabie S., Baxter A., Conroy R., Coote S.J., Craven A.P., Finch H., Hindley S., Kelly H.A., Lowdon A.W., McDonald E., Mitchell W.L., Pegg N.A., Procopiou P.A., Ramsden N.G., Thomas R., Walker D.A., Watson N.S., Jhoti H., Mooney C.J., Tang C.-M., Thomas P.J., Parry S., and Patel C. Bioorg. Med. Chem. Lett. 9 (1999) 1657
10. Nash H.W., Boatman D.L., and Long J.P. Toxicol. Appl. Pharmacol. 7 (1965) 25
11. Sheridan H., Lemon S., Frankish N., McArdle P., Higgins T., Jamse J.P., and Bhandari P. Eur. J. Med. Chem. 25 (1990) 603
12. Demir A.S., Aksoy-cam H., Camkertan N., Hamamct H., and Doǧanel F. Turk. J. Chem. 24 (2004) 141
13. Bailey W.F., and Ovaska T.V. In: Coxon J.M. (Ed). Advances in Detailed Reaction Mechanisms Vol. 3 (1994), JAI, Greenwich, CT 251-273
14. Bailey W.F., and Punzalan E.R. J. Am. Chem. Soc. 116 (1994) 6577
15. Giese B. Radical in Organic Synthesis (1986), Pergamon, New York, NY
16. Curran D.P. Synthesis (1988) 417 and 489
17. Giese B. Angew. Chem., Int. Ed. Engl. 28 (1989) 969
18. Curran D.P., Porter N.A., and Giese B. Stereochemistry of Radical Reactions (1995), VCH, New York, NY
19. Beckwith A.L.J., and Gerba S. Aust. J. Chem. 45 (1992) 289
20. Bailey W.F., Khanolkar A.D., Gavaskar K., Ovaska T.V., Rossi K., Thiel Y., and Wiberg K.B. J. Am. Chem. Soc. 113 (1991) 5720
21. Bailey W.F., Mealy M.J., and Wiberg K.B. Org. Lett. 4 (2002) 791
22. Suzuki D., Urabe H., and Sato F. J. Am. Chem. Soc. 123 (2001) 7925
23. Hanazawa T., Sasaki K., Takayama Y., and Sato F. J. Org. Chem. 68 (2003) 4980
24. Suzuki D., Tanaka R., Urabe H., and Sato F. J. Am. Chem. Soc. 124 (2002) 3518
25. Tanaka R., Nakano Y., Suzuki D., Urabe H., and Sato F. J. Am. Chem. Soc. 124 (2002) 9682
26. Sato F., Urabe H., and Okamoto S. Chem. Rev. 100 (2000) 2835
27. Sato F., and Okamoto S. Adv. Synth. Catal. 343 (2001) 759
28. Sato F., and Urabe H. In: Marek I. (Ed). Titanium and Zirconium in Organic Synthesis (2002), Wiley-VCH, Weinheim, Germany 319-354
29. Lautens M., and Mancuso J. Org. Lett. 4 (2002) 2105
30. Hoffmann R.W. Dehydrobenzene and Cycloalkynes (1967), Academic, New York, NY
31. Wakefield B.J. The Chemistry of Organolithium Compounds (1974), Pergamon, New York, NY
32. Bailey W.F., and Longstaff S.C. J. Org. Chem. 63 (1998) 432
33. Zhang L., and Herndon J.W. Organometallics 23 (2004) 1231
34. Ram V.J., and Goel A. Tetrahedron Lett. 37 (1996) 93
35. Ram V.J., Nath M., Srivastava P., Sarkhel S., and Maulik P.R. J. Chem. Soc., Perkin Trans. 1 (2000) 3719
36. Ram V.J., and Agarwal N. Tetrahedron Lett. 42 (2001) 7127
37. Ram V.J., and Srivastava P. J. Chem. Res., Synop. (2001) 421
38. Nath M., Srivastava P., Goel A., and Ram V.J. Eur. J. Org. Chem. (1998) 2083
39. Ram V.J., Agarwal N., Sharon A., and Maulik P.R. Tetrahedron Lett. 43 (2002) 307
40. Farhanullah, Agarwal N., Goel A., and Ram V.J. J. Org. Chem. 68 (2003) 2983
41. Sharon A., Pratap R., Maulik P.R., and Ram V.J. Tetrahedron 61 (2005) 3781
42. Ram V.J., Srivastava P., and Goel A. Tetrahedron 59 (2003) 7141
43. Srivastava P., Saxena A.S., and Ram V.J. Synthesis (2000) 541
44. Ram V.J., and Verma M. Indian J. Chem. 29B (1990) 624
45. Ram V.J., Verma M., Hussaini F.A., and Shoeb A. Liebigs Ann. Chem. (1991) 1229
46. Ram V.J., Singh S.K., Hussaini F.A., and Shoeb A. J. Chem. Res., Synop. (1993) 110
47. Ram V.J., Haque N., and Shoeb A. Sulfur Lett. 16 (1993) 165
48. Ram V.J., Mumtazuddin S., Pragya, Haque N., Hussaini F.A., Shoeb A., and Bhaduri A.P. J. Chem. Res., Synop. (1994) 354
49. Tominaga Y., Ushirogochi A., and Matsuda Y. J. Heterocycl. Chem. 24 (1987) 1557
50. Pratap R., Sil D., and Ram V.J. Tetrahedron Lett. 46 (2005) 5025
51. Goel A., Singh F.V., Dixit M., Verma D., Raghunandan R., and Maulik P.R. Chem. Asian J. 2 (2006) 239