Ultrasound assisted N-bromosuccinimde catalyzed one pot condensation approach for synthesis of Bis(indolyl)methanes from primary alcohols

Chhattise, P.; Handore, K.; Mohite, K.; Chabukswar, V.

Growing Science » Current Chemistry Letters » Ultrasound assisted N-bromosuccinimde catalyzed one pot condensation approach for synthesis of Bis(indolyl)methanes from primary alcohols

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Current Chemistry Letters

ISSN 1927-730x (Online) - ISSN 1927-7296 (Print) Quarterly Publication Volume 5 Issue 3 pp. 129-135 , 2016

Ultrasound assisted N-bromosuccinimde catalyzed one pot condensation approach for synthesis of Bis(indolyl)methanes from primary alcohols Pages 129-135 Download PDF

Authors: Prakash Chhattise, Kalpana Handore, Kakasaheb Mohite, Vasant Chabukswar

DOI: 10.5267/j.ccl.2016.5.001

Keywords: Indoles, N-Bromosuccinmide, Ultrasound, Bio(Indolyl)Methanes

Abstract: A simple, efficient protocol for one pot synthesis of bis(indolyl)methanes from primary alcohols is investigated with N-bromosuccinimde as a catalyst under ultrasound irradiation. Alcohols can be converted into carbonyl compounds by removal of hydrogen in presence of N-bromosuccinimde as an oxidant and can react in situ with indole to give desired bis(indolyl)methanes. In the reported one pot multicomponent condensation reaction N-bromosuccinimde promotes the oxidation of alcohol to aldehyde, facilitating the subsequent condensation with indole to afford bis(indolyl) methanes in good to excellent yields. The inexpensiveness and easy handling are some of important feature of N-bromosuccinimde. The by-product N-succinimide can be easily recovered and recycled to N-bromosuccinimide.

How to cite this paper

 Chhattise, P., Handore, K., Mohite, K & Chabukswar, V. (2016). Ultrasound assisted N-bromosuccinimde catalyzed one pot condensation approach for synthesis of Bis(indolyl)methanes from primary alcohols.Current Chemistry Letters, 5(3), 129-135.

Refrences

1. Sundberg R. J. (1996) The Chemistry of Indoles. Academic Press New York, USA.
2. Bell R., Carmeli S., and Sar N. (1994) Vibrindole A, a metabolite of the marine bacterium, vibrio parahaemolyticus, isolated from the toxic mucus of the Boxfish ostracion cubicus. J. Nat. Prod., 57 (11) 1587-1590.
3. Sujatha K., Perumal P. T., Muralidharan D., and Rajendra M. (2009) Synthesis, analgesicand anti-inflamatory activities of bis (indolyl) methanes. Indian J. Chem., 48B (2) 267- 272.
4. McDougal A., Gupta M. S., Morrow D. K., Ramamoorthy K., Lee J. E., and Safe S. H. (2001) Methyl‐substituted diindolylmethanes as inhibitors of estrogen‐induced growth of T47D cells and mammary tumors in rats. Breast Cancer Res. Trea., 66 (2) 147-157.
5. Safe S., Papineni S., and Chintharlapalli S. (2008) Cancer chemotherapy with indole-3-carbinol, bis(3'-indolyl)methane and synthetic analogs. Cancer Lett., 269 (2) 326-338.
6. Noland W. E., Venkiteswaran M. R., and Richards C. U. (1961) Cyclizative Condensations. I. 2-Methylindole with Acetone and Methyl Ethyl Ketone. J. Org. Chem., 26 (11), 4241-4248.
7. Babu G., Sridhar N., and Perumal P. T. (2000) A convenient method of synthesis of Bis-Indolylmethanes: Indium trichloride catalyzed reactions of indole with aldehydes and schiff's bases. Synth. Commun., 30 (9) 1609-1614.
8. Farhad S., Somayeh A., and Ali M. (2013) Rice-husk supported FeCl3 nanoparticles: Introduction of a mild efficient and reusable catalyst for some of the multicomponent reactions. C. R. Chimie, 16 (10) 945-955
9. (a)Yokoyama Y., Matsumoto T., and Murakami Y. (1995) Optically active total synthesis of clavicipitic acid. J. Org. Chem, 60 (6) 1486-1487. (b) Yang S D, Sun C. L., Fang Z., Li B. J., Li Y. Z., and Shi Z. J. (2008) Palladium-Catalyzed Direct Arylation of (Hetero)Arenes with Aryl Boronic Acids. Angew. Chem. Int. Ed, 47 (8) 1473-1476.
10. Prasanna T. R. S., and Mohanraju K. (2011) Polymer bromide-DMSO: novel reagent system for the Oxidation of alcohols to carbonyl compounds. Tetrahedron Lett., 52 (51) 6971-6973.
11. Collins J. C., Hess W. W., and Frank F. J. (1968) Dipyridine-chromium(VI) oxide oxidation of alcohols in dichloromethane. Tetrahedron Lett, 9 (30) 3363-3366.
12. Dess D. B., and Martin J. C. (1983) Readily accessible 12-I-5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem. 48 (22) 4155- 4156.
13. Ramchandran K., Muralidharan D., and Perumal P. T. (2011) Palladium catalyzed alkylation of indole via aliphatic C–H bond activation of tertiary amine. Tetrahedron Lett, 52 (28) 3579-3583.
14. Zhang S., Fan W., Qu H., Xiao C., Wang N., Shu l., Hu Q., and Liu L. (2012) One pot synthesis of Bis(indolyl)methanes: Ruthenium catalyzed reaction of benzyl alcohols and indoles. Curr. Org. Chem, 16, 942-948.
15. Guo X., Pan S., Liu J. and Li Z. (2009) One-pot synthesis of symmetric and unsymmetric 1,1-Bis-indolylmethanes via tandem iron-catalyzed C−H bond oxidation and C−O bond cleavage. J. Org. Chem., 74 (22) 8848-8851.
16. Nobuta T., Fujiya A., Tada N., Miura T. and Itoh A. (2012) One-pot synthesis of Bisindolylmethanes from benzyl alcohols and indoles using catalytic iodine and molecular oxygen under visible light irradiation. Synlett. (20) 2975-2979.
17. Hikawa H. and Yokoyama Y. (2013) Pd-catalyzed C–H activation in water: synthesis of bis (indolyl) ethanes from indoles and benzyl alcohols RSC Advances, 3, 1061-1064.
18. Bandgar B.P. and Shaikh K.A. (2003) Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions. Tetrahedron Lett., 44 (9) 1959-1961.
19. Shashidhara K.V., Kumar M., Sonkar R., Singh B.S., Khanna A. K., and Bhatia G. J. (2012) Indole-Based Fibrates as Potential Hypolipidemic and Antiobesity Agents. Med. Chem., 55 (6) 2769-2779.
20. Li J. T., Sun M. X., He G. Y., and Xu X. Y. (2011) Efficient and green synthesis of bis(indolyl)methanes catalyzed by ABS in aqueous media under ultrasound irradiation. Ultrason. Sonochem., 18 (1) 412-414.