Water-Mediated Green and Efficient Synthesis of Bis(Indolyl)methanes Using Ammonium Iron(II) Sulfate

Author(s): Vikas D. Kadu, Dinesh N. Nadimetla, Mahesh G. Hublikar, Dattatraya G. Raut, Raghunath B. Bhosale*

Journal Name: Letters in Organic Chemistry

Volume 17 , Issue 1 , 2020


Become EABM
Become Reviewer
Call for Editor

Graphical Abstract:


Abstract:

An efficient protocol for the synthesis of symmetrical 3,3’-bis(indolyl)arylmethanes catalyzed by green and easily available ammonium iron(II) sulfate (Mohr’s salt) has been developed in “green” water solvent afforded in excellent yield.

Keywords: Water, catalysis, Bis(indolyl)methanes, green chemistry, ammonium iron(II) sulfate, Indole.

[1]
Singh, T.P.; Singh, O.M. Mini-Reviews. Med. Chem., 2017, 18(1), 9-25.
[2]
Sharma, V.; Kumar, P.; Pathaka, D. J. Heterocycl. Chem., 2010, 47(3), 491-502.
[3]
Segraves, N.L.; Crews, P. J. Nat. Prod., 2005, 68(10), 1484-1488.
[4]
Praveen, P.J.; Parameswaran, P.S.; Majik, M.S. Synthesis, 2015, 47(13), 1827-1837.
[5]
Blunt, J.W.; Carroll, A.R.; Copp, B.R.; Davis, R.A.; Keyzers, R.A.; Prinsep, M.R. Nat. Prod. Rep., 2018, 35(1), 8-53.
[6]
Fahy, E.; Potts, B.C.M.; Faulkner, D.J.; Smith, K. J. Nat. Prod., 1991, 54(2), 564-569.
[7]
Bell, R.; Carmeli, S.; Sar, N.; Vibrindole, A. J. Nat. Prod., 1994, 57(11), 1587-1590.
[8]
Bifulco, G.; Bruno, I.; Riccio, R.; Lavayre, J.; Bourdy, G. J. Nat. Prod., 1995, 58(8), 1254-1260.
[9]
Oh, K.B.; Mar, W.; Kim, S.; Kim, J.Y.; Lee, T.H.; Kim, J.G.; Shin, D.; Sim, C.J. Shin. J. Biol. Pharm. Bull., 2006, 29(3), 570-573.
[10]
Porter, J.K.; Bacon, C.W.; Robbins, J.D.; Himmelsbach, D.S.; Higman, H.C. J. Agric. Food Chem., 1976, 25(1), 88-93.
[11]
Khuzhaev, B.U.; Aripova, S.F.; Shakirov, R.S. Chem. Nat. Compd., 1994, 30(5), 635-636.
[12]
Garbe, T.R.; Kobayashi, M.; Shimizu, N.; Takesue, N.; Ozawa, M.; Yukawa, H. J. Nat. Prod., 2000, 63(5), 596-598.
[13]
Imran, S.; Taha, M.; Ismail, N.H. Curr. Med. Chem., 2015, 22(38), 4412-4433.
[14]
Shiri, M.; Zolfigol, M.A.; Kruger, H.G.; Tanbakouchian, Z. Chem. Rev., 2010, 110(4), 2250-2293.
[15]
Hikawa, H.; Yokoyama, Y. RSC Advances, 2013, 3(4), 1061-1064.
[16]
Abe, T.; Nakamura, S.; Yanada, R.; Choshi, T.; Hibino, S.; Ishikura, M. Org. Lett., 2013, 15(14), 3622-3625.
[17]
Brahmachari, G.; Banerjee, B. ACS Sustain. Chem.& Eng., 2014, 2(12), 2802-2812.
[18]
Huo, C.; Wang, C.; Sun, C.; Jia, X.; Wang, X.; Chang, W.; Wu, M. Adv. Synth. Catal., 2013, 355(10), 1911-1916.
[19]
Lucarini, S.; Mari, M.; Piersanti, G.; Spadoni, G. RSC Advances, 2013, 3(41), 19135.
[20]
Zhuo, M.H.; Jiang, Y.J.; Fan, Y.S.; Gao, Y.; Liu, S.; Zhang, S. Org. Lett., 2014, 16(4), 1096-1099.
[21]
Mendes, S.R.; Thurow, S.; Penteado, F.; da Silva, M.S.; Gariani, R.A.; Perin, G.; Lenardão, E.J. Green Chem., 2015, 17(8), 4334-4339.
[22]
Lin, L.P.; Yuan, P.; Jiang, N.; Mei, Y.N.; Zhang, W.J.; Wu, H.M.; Zhang, A.H.; Cao, J.M.; Xiong, Z.X.; Lu, Y.; Tan, R.X. Org. Lett., 2015, 17(11), 2610-2613.
[23]
Mo, L.P.; Ma, Z.C.; Zhang, Z.H. Synth. Commun., 2005, 35(15), 1997-2004.
[24]
Silveira, C.C.; Mendes, S.R.; Líbero, F.M.; Lenardão, E.J.; Perin, G. Tetrahedron Lett., 2009, 50(44), 6060-6063.
[25]
Hasaninejad, A.; Zare, A.; Sharghi, H.; Arkivoc, K.N. -; 2007, U. ARKIVOC, 2007, 14, 39.
[26]
Firouzabadi, H.; Iranpoor, N.; Jafari, A.A. J. Mol. Catal. Chem., 2006, 244(1-2), 168-172.
[27]
Deb, M.L.; Bhuyan, P.J. Tetrahedron Lett., 2006, 47(9), 1441-1443.
[28]
Wang, L.; Han, J.; Tian, H.; Sheng, J.; Fan, Z.; Tang, X. Synlett, 2005, 2, 337-339.
[29]
Bandgar, B.P.; Bettigeri, S.V.; Joshi, N.S. Monatsh. Chem., 2004, 135(10), 1265-1273.
[30]
Ghorbani-Vaghei, R.; Veisi, H.; Keypour, H.; Dehghani-Firouzabadi, A.A. Mol. Divers., 2010, 14(1), 87-96.
[31]
Zhang, Z.H.; Yin, L.; Wang, Y.M. Synthesis (Stuttg), 2005, 12, 1949-1954.
[32]
Naidu, K.R.M.; Khalivulla, S.I.; Kumar, P.C.R.; Lasekan, O. Org. Commun., 2012, 5(3), 150-159.
[33]
Zhang, S.; Fan, W.; Qu, H.; Xiao, C.; Wang, N.; Shu, L.; Hu, Q.; Liu, L. Curr. Org. Chem., 2012, 16(7), 942-948.
[34]
Azizi, N.; Gholibeghlo, E. Manocheri. Z. Sci. Iran., 2012, 19(3), 574-578.
[35]
Happened, W. Chemistry of the Elements; Butterworth-Heinemann, E., Ed. , 1997. Vol. 25, pp. 1070-1112.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 17
ISSUE: 1
Year: 2020
Published on: 12 December, 2019
Page: [61 - 67]
Pages: 7
DOI: 10.2174/1570178616666190522121135
Price: $65

Article Metrics

PDF: 20
HTML: 3