Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2022; 54(05): 1347-1352
DOI: 10.1055/a-1668-9910
DOI: 10.1055/a-1668-9910
paper
Synthesis of Bis(indolyl)methanes through an Alkylation Reaction of Indoles with Sodium Alkoxides
We thank the National Natural Science Foundation of China (Nos. 22001231 and 21772176) and the Natural Science Foundation of Zhejiang Province (Nos. LQ20B020012 and LY20B020013) for financial support.
Abstract
We describe an alkylation reaction of indoles with sodium alkoxides for the synthesis of bis(indolyl)methanes. 1-Tetralone proved to be an efficient hydrogen acceptor, thus avoiding the use of precious transition metals such as Ru and Ir. This reaction features transition-metal-free conditions, uses readily available starting materials, and can be conducted on a gram scale.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1668-9910.
- Supporting Information
Publication History
Received: 14 September 2021
Accepted after revision: 14 October 2021
Accepted Manuscript online:
14 October 2021
Article published online:
18 November 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Chem. Rev. 2010; 110: 2250
- 1b Zhang M.-Z, Chen Q, Yang G.-F. Eur. J. Med. Chem. 2015; 89: 421
- 2a Bifulco G, Bruno I, Riccio R, Lavayre J, Bourdy G. J. Nat. Prod. 1995; 58: 1254
- 2b Sivaprasad G, Perumal PT, Prabavathy VR, Mathivanan N. Bioorg. Med. Chem. Lett. 2006; 16: 6302
- 2c Safe S, Papineni S, Chintharlapalli S. Cancer Lett. 2008; 269: 326
- 2d Ichite N, Chougule MB, Jackson T, Fulzele SV, Safe S, Singh M. Clin. Cancer Res. 2009; 15: 543
- 2e Bonnesen C, Eggleston IM, Hayes JD. Cancer Res. 2001; 61: 6120
- 2f Marrelli M, Cachet X, Conforti F, Sirianni R, Chimento A, Pezzi V, Michel S, Statti GA, Menichini F. Nat. Prod. Res. 2013; 27: 2039
- 2g Lee J. Nutr. Cancer 2019; 71: 992
- 3a Xia M, Wang S.-h, Yuan W.-b. Synth. Commun. 2004; 34: 3175
- 3b Babu G, Sridhar N, Perumal PT. Synth. Commun. 2000; 30: 1609
- 3c Xu X.-F, Xiong Y, Ling X.-G, Xie X.-M, Yuan J, Zhang S.-T, Song Z.-R. Chin. Chem. Lett. 2014; 25: 406
- 3d Kothandapani J, Ganesan A, Vairaprakash P, Ganesan SS. Tetrahedron Lett. 2015; 56: 2238
- 3e Griffiths K, Kumar P, Akien GR, Chilton NF, Abdul-Sada A, Tizzard GJ, Coles SJ, Kostakis GE. Chem. Commun. 2016; 52: 7866
- 3f Qiao J, Gao S, Wang L, Wei J, Li N, Xu X. J. Organomet. Chem. 2020; 906: 121039
- 4a Li WJ, Lin XF, Wang J, Li GL, Wang YG. Synth. Commun. 2006; 35: 2765
- 4b El-Sayed M, Mahmoud K, Hilgeroth A. Curr. Chem. Lett. 2014; 3: 7
- 4c Nasreen A, Varala R, Rao KS. Org. Commun. 2017; 10: 104
- 5a Tabatabaeian K, Mamaghani M, Mahmoodi N, Khorshidi A. Can. J. Chem. 2006; 84: 1541
- 5b Mendes sR, Thurow S, Penteado F, da Silva MS, Gariani RA, Perin G, Lenardão EJ. Green Chem. 2015; 17: 4334
- 5c Patil VD, Patil KP, Sutar NR, Gidh PV. Int. J. Chem. Sci. 2015; 13: 857
- 6a Chen L, Wang C, Zhou L, Sun J. Adv. Synth. Catal. 2014; 356: 2224
- 6b Nemallapudi BR, Zyryanov GV, Avula B, Guda MR, Cirandur SR, Venkataramaiah C, Rajendra W, Gundala S. Bioorg. Chem. 2019; 87: 465
- 6c Mathavan S, Kannan K, Yamajala RB. R. D. Org. Biomol. Chem. 2019; 17: 9620
- 6d Alegre-Requena JV, Valero-Tena A, Sonsona IG, Uriel S, Herrera RP. Org. Biomol. Chem. 2020; 18: 1594
- 6e Mitra B, Ghosh P. ChemistrySelect 2021; 6: 68
- 7a Wang A, Liu X, Su Z, Jing H. Catal. Sci. Technol. 2014; 4: 71
- 7b Esmaielpour M, Akhlaghinia B, Jahanshahi RJ. Chem. Sci. 2017; 129: 313
- 7c Bahuguna A, Kumar S, Sharma V, Reddy KL, Bhattacharyya K, Ravikumar PC, Krishnan V. ACS Sustainable Chem. Eng. 2017; 5: 8551
- 7d Li D, Wang J, Chen F, Jing H. RSC Adv. 2017; 7: 4237
- 7e Khatab TK, Abdelghany AM, Soliman HA. Silicon 2018; 10: 703
- 7f Bahuguna A, Kumar S, Krishnan V. 2018; 3: 314
- 7g Wu Z, Wang G, Yuan S, Wu D, Liu W, Ma B, Bi S, Zhan H, Chen X. Green Chem. 2019; 21: 3542
- 7h Hajibabaei M, Senejani MA, Shafiei F. Appl. Organomet. Chem. 2020; 34: e5641
- 8 Nobuta T, Fujiya A, Tada N, Miura T, Itoh A. Synlett 2012; 23: 2975
- 9 Badigenchala S, Ganapathy D, Das A, Singh R, Sekar G. Synthesis 2014; 46: 101
- 10 Hosseinzadeh-Khanmiri R, Kamel Y, Keshvari Z, Mobaraki A, Shahverdizadeh GH, Vessally E, Babazadeh M. Appl. Organomet. Chem. 2018; 32: e4452
- 11 Nguyen N.-K, Ha M.-T, Bui HY, Trinh QT, Tran BN, Nguyen VT, Hung TQ, Dang TT, Vu XH. Catal. Commun. 2021; 149: 106240
- 12a Suda K, Takanami T. Chem. Lett. 1994; 1915
- 12b Veisi H, Ataee M, Fatolahi L, Lotfi S. Lett. Org. Chem. 2013; 10: 111
- 12c Fu Y, Lu Z, Fang K, He X, Xu H, Hu Y. RSC Adv. 2020; 10: 10848
- 13a Hamid MH. S. A, Slatford PA, Williams JM. J. Adv. Synth. Catal. 2007; 349: 1555
- 13b Nixon TD, Whittlesey MK, Williams JM. J. Dalton Trans. 2009; 753
- 13c Dobereiner GE, Crabtree RH. Chem. Rev. 2010; 110: 681
- 13d Garg N, Sarkar A, Sundararaju B. Coord. Chem. Rev. 2021; 443: 213728
- 14a Zhang S, Fan W, Qu H, Xiao C, Wang N, Shu L, Hu Q, Liu L. Curr. Org. Chem. 2012; 16: 942
- 14b Putra AE, Takigawa K, Tanaka H, Ito Y, Oe Y, Ohta T. Eur. J. Org. Chem. 2013; 6344
- 14c Biswas N, Sharma R, Srimani D. Adv. Synth. Catal. 2020; 362: 2902
- 15a Whitney S, Grigg R, Derrick A, Keep A. Org. Lett. 2007; 9: 3299
- 15b Qiang W, Liu X, Loh T.-P. ACS Sustainable Chem. Eng. 2019; 7: 8429
- 16a Djerassi C. Org. React. 1951; 6: 207
- 16b Procter G. In Comprehensive Organic Synthesis . Trost BM, Fleming I. Pergamon; Oxford: 1991: 305
- 16c de Graauw CF, Peters JA, van Bekkum H, Huskens J. Synthesis 1994; 1007
- 17 Ouali A, Majoral J.-P, Caminade A.-M, Taillefer M. ChemCatChem 2009; 1: 504
- 18 Ramachandiran K, Muralidharan D, Perumal PT. Tetrahedron Lett. 2011; 52: 3579
- 19 Mulla SA. R, Sudalai A, Pathan MY, Siddique SA, Inamdar SM, Chavan SS, Reddy RS. RSC Adv. 2012; 2: 3525
- 20 Srivastava A, Patel SS, Chandna N, Jain N. J. Org. Chem. 2016; 81: 11664
- 21 Liu X, Ma S, Toy PH. Org. Lett. 2019; 21: 9212
- 22 Shelke GM, Rao VK, Tiwari RK, Chhikara BS, Parang K, Kumar A. RSC Adv. 2013; 3: 22346
- 23 Griffiths K, Kumar P, Akien GR, Chilton NF, Abdul-Sada A, Tizzard GJ, Coles SJ, Kostakis GE. Chem. Commun. 2016; 52: 7866
- 24 Roy SR, Nijamudheen A, Pariyar A, Ghosh A, Vardhanapu PK, Mandal PK, Datta A, Mandal SK. ACS Catal. 2014; 4: 4307