Synthesis of 3-Aminoalkylated Indoles Using Heterogeneous MgFe₂O₄ Nanoparticles Under Microwave Irradiation in One-Pot Three-Component System

Abstract

A series of 3-aminoalkylated indoles are efficiently synthesised in a one-pot three-component reaction under microwave irradiation. Magnesium ferrite (MgFe₂O₄) nanoparticles (10 mol%) have been used as heterogeneous catalyst, which may easily be recovered by application of an external magnet and the recovered catalyst can be reused at least for five runs without affecting the efficiency of the catalyst. The solvent-free protocol developed has advantages of less reaction time, high yields, and easy workup, and the protocol is applicable to various acid base sensitive functional groups present in the substrate. The reported methodology is highly suitable especially for primary amines in addition to secondary amines as one of the components.

Key words

heterogeneous catalyst - 3-aminoalkylated indoles - solvent-free protocol - microwave-assisted - multicomponent reaction - one-pot synthesis

• References

• 1a Khan IA, Saxena AK. Tetrahedron 2012; 68: 294

For recent reviews, see:
• 1b Dömling A. Chem. Rev. 2006; 106: 17
• 1c Dömling A, Wang W, Wang K. Chem. Rev. 2012; 112: 3083
• 1d Shiri M. Chem. Rev. 2012; 112: 3508
• 1e Eckert H. Molecules 2012; 17: 1074
• 1f de Graaff C, Ruijter E, Orru RV. A. Chem. Soc. Rev. 2012; 41: 3969
• 1g Kumar A, Kumar M, Gupta MK. Tetrahedron Lett. 2009; 50: 7024
• 1h Bienaymé H, Hulme C, Oddon G, Schmitt P. Chem. Eur. J. 2000; 6: 3321
• 1i Srihari P, Singh VK, Bhunia DC, Yadav JS. Tetraheron Lett. 2009; 50: 3763
• 2a Pirrung MC, Sarma KD. J. Am. Chem. Soc. 2004; 126: 444
• 2b Ollevier T, Nadeau E, Guay-Begin A-A. Tetrahedron Lett. 2006; 47: 8351
• 2c Brogan AP, Dickerson TJ, Janda KD. Angew. Chem. Int. Ed. 2006; 45: 8100
• 2d Butler RN, Coyne AG. Chem. Rev. 2010; 110: 6302
• 2e Gu Y. Green Chem. 2012; 14: 2091
• 2f Lindstrom UM. Chem. Rev. 2002; 102: 2751
• 2g Kumar A, Kumar M, Gupta MK. Green Chem. 2012; 14: 2677
• 3a Welton T. Chem. Rev. 1999; 99: 2071
• 3b Wesserscheid P, Keim W. Angew. Chem. Int. Ed. 2000; 39: 3772
• 3c Sheldon R. Chem. Commun 2001; 2399
• 3d Kumar A, Gupta MK, Srivastava S. Green Chem. 2011; 13: 2459
• 4a Raston CL, Scott JL. Green Chem. 2000; 2: 49
• 4b Kumar A, Sharma S. Green Chem. 2011; 13: 2017
• 4c Martins MA. P, Frizzo CP, Moreira DN, Buriol P, Machado P. Chem. Rev. 2009; 109: 4140
• 4d Nagaiah K, Sreenu D, Srinivasa RR, Vashishta G, Yadav JS. Tetrahedron Lett. 2006; 47: 4409
• 5 For a recent review of indole containing natural products, see: Faulkner D. Nat. Prod. Rep. 1999; 16: 155
• 6a Wynne JH, Stalick WM. J. Org. Chem. 2002; 67: 5850
• 6b Kumar A, Sharma S, Maurya RA. Tetrahedron Lett. 2009; 50: 5937
• 6c Kochanowska-Karamyan AJ, Hamann MT. Chem. Rev. 2010; 110: 4489
• 7 Qu Y, Ke F, Zhou L, Li Z, Xiang H, Wu D, Zhou X. Chem. Commun. 2011; 47: 3912
• 8 Anselmo D, Escudero-Adan EC, Belmonte MM, Kleij AW. Eur. J. Inorg. Chem. 2012; 4694
• 9 Chen W, Cai Y, Fu X, Liu L, Lin X, Feng X. Org. Lett. 2011; 13: 4910
• 10 Singh N, Allam BK, Raghuvanshi DS, Singh KN. Adv. Synth. Catal. 2013; 355: 1840
• 11a Crawford DE. Beilstein J. Org. Chem. 2017; 13: 1850
• 11b Rajesh UC, Wang J, Prescott S, Tsuzuki T, Rawat DS. ACS Sustainable Chem. Eng. 2015; 3: 9
• 12 Rahimizadeh M, Eshghi H, Mokaber-Esfahani M, Gholizadeh M. J. Chin. Chem. Soc. 2014; 61: 192
• 13a Bansal S, Singh PP. Chem. Chem. Technol. 2019; 13: 18
• 13b Parveen P, Singh PP. Orient. J. Chem. 2017; 33: 4
• 14 Bansal S, Kumar Y, Das DK, Singh PP. Chem. Chem. Technol. 2019; 13: 163
• 15 Goswami V, Thorat PB, Kadam VN, Khiste SA, Bhusare SR. Chin. Chem. Lett. 2013; 24: 422
• 16 Aghaalikhani S, Behbahani FK. Chemistry Select 2016; 1: 5530
• 17 Rao KV, Rao MS, Jain N, Panwar J, Kumar A. Org. Med. Chem. Lett. 2011; 1: 10
• 18 Ramarajan R, Ramalingam A, Duraisamy C, Sambandam S, Noureddine N, Al-Dossary OM, Bousiakoug LG. J. King Saud Univ. Sci. 2023; 35: 102475