Synthesis of 2-Indolyl-1-nitroalkane derivatives using nanocrystalline titanium(iv) oxide

Synthetic Communications

Volumn 39, Issue 22, 2009, Pages 4100-4108

  Kantam, M Lakshmi ^a   Laha, Soumi ^a   Yadav, Jagjit ^a   Srinivas, P ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2 indolyl 1 nitroalkane; Friedel Crafts alkylation; Heterogeneous catalysis; Nanocrystalline titanium(IV) oxide

Indexed keywords

2 INDOLYL 1 NITROALKANE DERIVATIVE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; INDOLE DERIVATIVE; NANOCRYSTAL; NITROALKENE DERIVATIVE; TITANIUM DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CENTRIFUGATION; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; FRIEDEL CRAFTS REACTION; ISOMER; RECYCLING; ROOM TEMPERATURE;

EID: 70350676693     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910902883728     Document Type: Article

References (35)

1. Olah, G. A.; Krishnamurty, R.; Prakash, G. K. S. Friedel-Crafts alkylation; In Comprehensive Organic Synthesis; B. M. Trost, I. Fleming (Eds.); Pergamon: Oxford, 1991; vol.3, pp. 293-339.
2. Takano S.,Ogasawara K. The Alkaloids: Chemistry and Pharmacology; A. Brossi (Ed.); Aacademic Press: New York 1989, vol. 36, ch. 5, pp. 225-251.
3. Greig, N. H.; Pei, X. F.; Soncrant, T. T.; Ingram, D. K.; Brossi, A. Phenserine and ring C hetero-analogues: Drug candidates for the treatment of Alzheimer's disease. Med. Res. Rev. 1995, 15, 3-31.
4. Yamaguchi, M.; Igarashi, Y.; Reddy, R. S.; Shiraishi, T.; Hirama, M. Asymmetric Michael addition of nitroalkanes to prochiral acceptors catalyzed by proline rubidium salts. Tetrahedron 1997, 53, 11223-11236.
5. Ono, N. The Nitro Group in Organic Synthesis; Wiley-VCH: New York, 2001.
6. Manabe, K.; Aoyama, N.; Kobayashi, S. Friedel-Crafts-type conjugate addition of indoles using a lewis acid-surfactant-combined catalyst in water. Adv. Synth. Catal. 2001, 343, 174-176
7. Alam, M. M.; Varala, R.; Adapa, S. R. Conjugate addition of indoles and thiols with electron-deficient olefins catalyzed by Bi(OTf)3. Tetrahedron Lett. 2003, 44, 5115-5119
8. Bartoli, G.; Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcantoni, E.; Sambri, L.; Torregiani, E. Efficient preparation of 2-inolyl-1-nitroalkane derivatives employing nitroalkenes as versatile michael acceptors: New practical linear approach to alkyl 9H-b-carboline-4-carboxylate. J. Org. Chem. 2005, 70, 1941-1944
9. Bandini, M.; Fagioli, M.; Umani-Ronchi, A. Solid acid-catalysed michael-type conjugate addition of indoles to electron-poor C=C bonds: Towards high atom economical semicontinuous processes. Adv. Synth. Catal. 2004, 346, 545-548.
10. Ballini, R.; Clemente, R. R.; Palmieri, A.; Petrini, M. Conjugate addition of indoles to nitroalkenes promoted by basic alumina in solventless conditions. Adv. Synth. Catal. 2006, 348, 191-196.
11. Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F. The facile and efficient Michael addition of indoles and pyrrole to a,b-unsaturated electron-deficient compounds catalyzed by aluminium dodecyl sulfate trihydrate [Al(DS)3] ■ 3H2O in water. Chem. Commun. 2005, 789-791.
12. Jia, Y.-X.; Zhu, S.-F.; Yang, Y.; Zhou, Q.-L. Asymmetric Friedel-Crafts alkylations of indoles with nitroalkenes catalyzed by Zn(ii)-bisoxazoline complexes. J. Org. Chem. 2006, 71, 75-80
13. Singh, P. K.; Bisai, A.; Singh, V. K. Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by a bis(oxazoline)-Cu(II) complex. Tetrahedron Lett. 2007, 48, 1127-1129
14. Bandini, M.; Garelli, A.; Rovinetti, M.; Tommasi, S.; Umani-Ronchi, A. Catalytic enantioselective addition of indoles to arylni-troalkenes: An effective route to enantiomerically enriched tryptamine precursors. Chirality 2005, 17, 522-529; (d) Lu, S.-F.; Du, D.-M.; Xu, J.
15. Enantioselective Friedel-Crafts alkylation of indoles with nitroalkenes catalyzed by bifunctional tridentate bis(oxazoline)-Zn(II) complex. Org. Lett. 2006, 8, 2115-2118.
16. Herrera, R. P.; Sgarzani, V.; Bernardi, L.; Ricci, A. Catalytic enantiose-lective Friedel-Crafts alkylation of indoles with nitroalkenes by using a simple thiourea organocatalyst. Angew. Chem. Int. Ed. 2005, 44 6576-6579
17. Zhuang, W.; Hazell, R. G.; Jørgensen, K. A. Enantioselective Friedel-Crafts type addition of indoles to nitro-olefins using a chiral hydrogen-bonding catalyst-synthesis of optically active tetrahydro-b-carbolines. Org. Biomol. Chem. 2005, 3, 2566-2571.
18. Jiang, Y.; Decker, S.; Mohs, C.; Klabunde, K. J. Catalytic solid state reactions on the surface of nanoscale metal oxide particles. J. Catal. 1998, 180, 24-35
19. Lucas, E.; Decker, S.; Khaleel, A.; Seitz, A.; Fultz, S.; Ponce, A.; Li, W.; Carnes, C.; Klabunde, K. J. Nanocrystalline metal oxides as unique chemical reagents=sorbents. Chem. Eur. J. 2001, 7, 2505-2510.
20. Schlogl, R.; Abd Hamid, S. B. Nanocatalysis: Mature science revisited or something really new? Angew. Chem., Int. Ed. 2004, 43, 1628-1637
21. Choudary, B. M.; Ranganath, K. V. S.; Yadav, J.; Kantam, M. L. Synthesis of flavanones using nanocrystalline MgO. Tetrahedron Lett. 2005, 46, 1369-1371
22. Kantam, M. L.; Laha, S.; Yadav, J.; Choudary, B. M.; Sreedhar, B. Nanocrystalline titanium(IV) oxide as an efficient heterogeneous catalyst for tandem michael and nucleophilic 1,2-addition to enones. Adv. Synth. Catal. 2006, 348, 867-872
23. Kantam, M. L.; Laha, S.; Yadav, J.; Sreedhar, B. Friedel-Crafts alkylation of indoles with epoxides catalyzed by nanocrystal-line titanium(IV) oxide. Tetrahedron Lett. 2006, 47, 6213-6216
24. Choudary, B. M.; Ranganath, K. V. S.; Pal, U.; Kantam, M. L.; Sreedhar, B. Nanocrys-talline MgO for asymmetric henry and michael reactions. J. Am. Chem. Soc. 2005, 127, 13167-13171.
25. Choudary, B. M.; Mulukutla, R. S.; Klabunde, K. J. Benzylation of aromatic compounds with different crystallites of MgO. J. Am. Chem. Soc. 2003, 125, 2020-2021
26. Richards, R.; Li, W.; Decker, S.; Davidson, C.; Koper, O.; Zaikovski, V.; Volodin, A.; Rieker, T.; Klabunde, K. J. Consolidation of metal oxide nanocrystals. Reactive pellets with controllable pore structure that represent a new family of porous, inorganic materials. J. Am. Chem. Soc. 2000, 122, 4921-4925.
27. Kantam, M. L.; Laha, S.; Yadav, J.; Likhar, P. R.; Sreedhar, B.; Choudary, B. M. Asymmetric hydrosilylation of prochiral ketones catalyzed by nano-crystalline copper(II) oxide. Adv. Synth. Catal. 2007, 349, 1797-1802.
28. Bosh, H.; Janssen, F. Formation and control of nitrogen oxides. Catal. Today 1988, 2, 369-379
29. Forzatti, P. Environmental catalysis for stationary applications. Catal. Today 2000, 62, 51-65
30. Hoffmann, M. R.; Martin, S. T.; Choi, W.; Bahnemann, D. W. Environmental applications of semiconductor photocatalysis. Chem. Rev. 1995, 95, 69-96
31. Maldotti, A.; Molinari, A.; Amadelli, R. Photocatalysis with organized systems for the oxofunctionalization of hydrocarbons by O2. Chem. Rev. 2002, 102, 3811-3836.
32. Kantam, M. L.; Yadav, J.; Laha, S.; Sreedhar, B.; Jha, S. N-arylation of heterocycles with activated chloro-and flouroarenes using nanocrystalline copper(II) oxide. Adv. Synth. Catal. 2007, 349, 1938-1942
33. Kantam, M. L.; Ranganath, K. V. S.; Mahendar, K.; Chakrapani, L.; Choudary, B. M. Asymmetric Michael addition of malonates to enones catalyzed by nanocrys-talline MgO. Tetrahedron Lett. 2007, 48, 7646-7649.
34. Kantam, M. L.; Mahendar, K.; Sreedhar, B.; Choudary, B. M. Synthesis of a-amino nitriles through Strecker reaction of aldimines and ketoimines by using nanocrystal-line magnesium oxide. Tetrahedron 2008, 64 3351-3360
35. Kantam, M. L.; Laha, S.; Yadav, J.; Bhargava, S. An efficient synthesis of propargylamines via three-component coupling of aldehydes, amines, and alkynes catalyzed by nanocrystalline copper(II) oxide. Tetrahedron Lett. 2008, 49, 3083-3086.