Iron-Catalyzed Oxidative Coupling of Benzylamines and Indoles: Novel Approach for Synthesis of Bis(indolyl)methanes

Kovuru Gopalaiah; Sankala Naga Chandrudu; Alka Devi

doi:10.1055/s-0034-1380012

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(12): 1766-1774
DOI: 10.1055/s-0034-1380012

paper

Iron-Catalyzed Oxidative Coupling of Benzylamines and Indoles: Novel Approach for Synthesis of Bis(indolyl)methanes

Kovuru Gopalaiah*

Department of Chemistry, University of Delhi, Delhi 110007, India eMail: gopal@chemistry.du.ac.in

,

Sankala Naga Chandrudu

Department of Chemistry, University of Delhi, Delhi 110007, India eMail: gopal@chemistry.du.ac.in

,

Alka Devi

Department of Chemistry, University of Delhi, Delhi 110007, India eMail: gopal@chemistry.du.ac.in

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

Abstract

A novel route for synthesis of bis(indolyl)methanes has been developed by the oxidative coupling of benzylamines and indoles in the presence of iron(II) triflate as a catalyst and molecular oxygen as an oxidant. This method promises versatility, cost-effectiveness, and efficiency.

Key words

oxidative coupling - benzylamine - bis(indolyl)methane - iron(II) triflate - molecular oxygen

Volltext

Referenzen

References

1a Sundberg RJ. The Chemistry of Indoles . Academic; New York: 1996
1b Hibino S, Chozi T. Nat. Prod. Rep. 2001; 18: 66

2 Morris SA, Anderson RJ. Tetrahedron 1990; 46: 715

3a Ramirez A, Garcia Rubio S. Curr. Med. Chem. 2003; 10: 1891
3b Tjalkens RB, Safe S. US 8580843, 2013

4a Porter JK, Bacon CW, Robbins JD, Himmelsbach DS, Higman HC. J. Agric. Food Chem. 1997; 25: 88
4b Garbe TR, Kobayashi M, Shimizu N, Takesue N, Ozawa M, Yukawa H. J. Nat. Prod. 2000; 63: 596
4c Oh KB, Mar W, Kim S, Kim JY, Lee TH, Kim JG, Shin D, Sim CJ, Shin J. Biol. Pharm. Bull. 2006; 29: 570
4d Fahy E, Potts BC. M, Faulkner DJ, Smith K. J. Nat. Prod. 1991; 54: 564

5 Bell R, Carmeli S, Sar N. J. Nat. Prod. 1994; 57: 1587 ; and references cited therein
6 Shankar M, Suvetha K, Kumarasamyraja D, Gowrishankar NL. Int. J. Pharm. Pharm. Sci. 2012; 4: 518

7a Michnovics JJ, Bradlow HL In Food Phytochemicals I: Fruits and Vegetables, ACS Symposium Series 546. Huang M.-T, Osawa T, Ho C.-T, Rosen RT. American Chemical Society; Washington DC: 1993: 282
7b Zeligs MA. J. Med. Food 1998; 1: 67

8a Bell MC. Gynecol. Oncol. 2000; 78: 123
8b Thomas CH. US 4500689, 1985

9 Kalla RM. N, John JV, Park H, Kim I. Catal. Commun. 2014; 57: 55 ; and references cited therein

10a Nobuta T, Fujiya A, Tada N, Miura T, Itoh A. Synlett 2012; 23: 2975
10b Zhang S, Fan W, Qu H, Xiao C, Wang N, Shu L, Hu Q, Liu L. Curr. Org. Chem. 2012; 16: 942
10c Putra AE, Takigawa K, Tanaka H, Ito Y, Oe Y, Ohta T. Eur. J. Org. Chem. 2013; 6344

For representative reviews on iron catalysis, see:

11a Gopalaiah K. Chem. Rev. 2013; 113: 3248
11b Darwish M, Wills M. Catal. Sci. Technol. 2012; 2: 243
11c Junge K, Schröder K, Beller M. Chem. Commun. 2011; 47: 4849
11d Morris RH. Chem. Soc. Rev. 2009; 38: 2282
11e Bolm C. Nat. Chem. 2009; 1: 420
11f Correa A, García Mancheño O, Bolm C. Chem. Soc. Rev. 2008; 37: 1108
11g Bauer EB. Curr. Org. Chem. 2008; 12: 1341
11h Bolm C, Legros J, Le Paih J, Zani L. Chem. Rev. 2004; 104: 6217

12 Ji S.-J, Zhou M.-F, Gu D.-G, Jiang Z.-Q, Loh T.-P. Eur. J. Org. Chem. 2004; 1584
13 Wang S.-Y, Ji S.-J. Synth. Commun. 2008; 38: 1291
14 Sheikhshoaie I, Khabazzadeh H, Saeid-Nia S. Transition Met. Chem. (Dordrecht, Neth.) 2009; 34: 463
15 Veisi H, Maleki B, Eshbala FH, Veisi H, Masti R, Ashrafi SS, Baghayeri M. RSC Adv. 2014; 4: 30683
16 Gopalaiah K, Chandrudu SN. RSC Adv. 2015; 5: 5015

17a Cho SD, Yoon K, Chintharlapalli S, Abdelrahim M, Lei P, Hamilton S, Khan S, Ramaiah SK, Safe S. Cancer Res. 2007; 67: 674
17b Cho SD, Lee S.-O, Chintharlapalli S, Abdelrahim M, Khan S, Yoon K, Kamat AM, Safe S. Mol. Pharmacol. 2010; 77: 396

18 Lee S.-O, Li X, Hedrick E, Jin U.-H, Tjalkens RB, Backos DS, Li L, Zhang Y, Wu Q, Safe S. Mol. Endocrinol. 2014; 28: 1729
19 Vanderlaag K, Su Y, Frankel AE, Burghardt RC, Barhoumi R, Chadalapaka G, Jutooru I, Safe S. BMC Cancer 2010; 10: 669 ; http://www.biomedcentral.com/bmccancer
20 Tayebee R, Amini MM, Abdollahi N, Aliakbari A, Rabiei S, Ramshini H. Appl. Catal., A 2013; 468: 75
21 Kodama S, Yoshida J, Nomoto A, Ueta Y, Yano S, Ueshima M, Ogawa A. Tetrahedron Lett. 2010; 51: 2450
22 Bandgar BP, Patil AV, Kamble VT. ARKIVOC 2007; (xvi): 252
23 Liao B.-S, Chen J.-T, Liu S.-T. Synthesis 2007; 3215
24 Firouzabadi H, Iranpoor N, Jafari AA. J. Mol. Catal. A: Chem. 2006; 244: 168
25 Ghorbani-Vaghei R, Veisi H, Keypour H, Dehghani-Firouzabadi AA. Mol. Divers. 2010; 14: 87
26 Tribhuvannathji KV, Pandurang BB, Narayanrao BS. Chin. J. Chem. 2007; 25: 13
27 Ghorbani-Vaghei R, Malaekehpoor SM. Org. Prep. Proced. Int. 2010; 42: 175
28 Zare A, Parhami A, Moosavi-Zare AR, Hasaninejad A, Khalafi-Nezhad A, Beyzavi MH. Can. J. Chem. 2009; 87: 416
29 Xu H.-Y, Zi Y, Xu X.-P, Wang S.-Y, Ji S.-J. Tetrahedron 2013; 69: 1600
30 Yang Q, Yin ZL, Ouyang BL, Peng YY. Chin. Chem. Lett. 2011; 22: 515
31 Zahran M, Abdin Y, Salama H. ARKIVOC 2008; (xi): 256

Zusatzmaterial

Supporting Information