Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

K2CO3-Promoted Highly Selective N-Hydroxymethylation of Indoles Under Metal- and Lewis Acid-Free Conditions

Author(s): Xiao-Yu Zhou* and Xia Chen

Volume 18, Issue 2, 2021

Published on: 28 July, 2020

Page: [160 - 165] Pages: 6

DOI: 10.2174/1570178617999200728214752

Price: $65

Open Access Journals Promotions 2
Abstract

Inorganic base promoted highly selective N-hydroxymethylation of indole and its derivatives have been developed. It provided a simple method for the preparation of N-hydroxymethyl indoles with polyformaldehyde as reagents under the metal- and Lewis acid-free reaction conditions. The reaction proceeded smoothly using K2CO3 as base in 1,4-dioxane to produce the corresponding N-hydroxymethyl indoles with 62%->99% yields.

Keywords: Indoles, hydroxymethylation, polyformaldehyde, base-promoted, functionalization, highly selective.

« Previous Next »
Graphical Abstract

[1]
(a)Chang, K.J.; Moon, D.; Lah, M.S.; Jeong, K-S. Angew. Chem. Int. Ed., 2005, 44, 7926-7929.
[http://dx.doi.org/10.1002/anie.200503121]
(b)Kochanowska-Karamyan, A.J.; Hamann, M.T. Chem. Rev., 2010, 110(8), 4489-4497.
[http://dx.doi.org/10.1021/cr900211p] [PMID: 20380420]
(c)Tietze, L.F.; Sieber, T.A. Angew. Chem. Int. Ed., 2013, 52, 5447-5449.
[http://dx.doi.org/10.1002/anie.201301923]
(d)Lancianesi, S.; Palmieri, A.; Petrini, M. Chem. Rev., 2014, 114(14), 7108-7149.
[http://dx.doi.org/10.1021/cr400676v] [PMID: 24905229]
(e)Abouzeid, S.; Beutling, U.; Surup, F.; Abdel Bar, F.M.; Amer, M.M.; Badria, F.A.; Yahyazadeh, M.; Brönstrup, M.; Selmar, D. J. Nat. Prod., 2017, 80(11), 2905-2909.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00424] [PMID: 29131648]
(f)Zheng, C.J.; Bai, M.; Zhou, X.M.; Huang, G.L.; Shao, T.M.; Luo, Y.P.; Niu, Z.G.; Niu, Y.Y.; Chen, G.Y.; Han, C.R. J. Nat. Prod., 2018, 81(4), 1045-1049.
[http://dx.doi.org/10.1021/acs.jnatprod.7b00673] [PMID: 29489361]
(g)Yudinaa, L.N.; Bergman, J. Tetrahedron, 2003, 59, 1265-1275.
[http://dx.doi.org/10.1016/S0040-4020(03)00029-2]
(h)Liou, J-P.; Wu, C-Y.; Hsieh, H-P.; Chang, C-Y.; Chen, C-M.; Kuo, C-C.; Chang, J-Y. J. Med. Chem., 2007, 50(18), 4548-4552.
[http://dx.doi.org/10.1021/jm070557q] [PMID: 17685504]
(i)Kemnitzer, W.; Drewe, J.; Jiang, S.; Zhang, H.; Crogan-Grundy, C.; Labreque, D.; Bubenick, M.; Attardo, G.; Denis, R.; Lamothe, S.; Gourdeau, H.; Tseng, B.; Kasibhatla, S.; Cai, S.X. J. Med. Chem., 2008, 51(3), 417-423.
[http://dx.doi.org/10.1021/jm7010657] [PMID: 18197614]
[2]
(a)Guchhait, S.K.; Chaudhary, V.; Rana, V.A.; Priyadarshani, G.; Kandekar, S.; Kashyap, M. Org. Lett., 2016, 18(7), 1534-1537.
[http://dx.doi.org/10.1021/acs.orglett.6b00244] [PMID: 26986450]
(b)Kong, L.; Wang, M.; Zhang, F.; Xu, M.; Li, Y. Org. Lett., 2016, 18(23), 6124-6127.
[http://dx.doi.org/10.1021/acs.orglett.6b03131] [PMID: 27934344]
(c)Zhou, X.Y.; Chen, X.; Wang, L.G. Synlett, 2016, 27, 2742-2746.
[http://dx.doi.org/10.1055/s-0036-1588069]
(d)Yarlagadda, S.; Ramesh, B.; Ravikumar Reddy, C.; Srinivas, L.; Sridhar, B.; Subba Reddy, B.V. Org. Lett., 2017, 19(1), 170-173.
[http://dx.doi.org/10.1021/acs.orglett.6b03473] [PMID: 28009174]
(e)Zhou, X-Y.; Chen, X.; Wang, L-G. Synthesis, 2017, 49, 3662-3669.
[http://dx.doi.org/10.1055/s-0036-1589032]
(f)Zhou, X-Y.; Chen, X.; Wang, L-G.; Yang, D.; Li, J-H. Synlett, 2018, 29, 835-839.
[http://dx.doi.org/10.1055/s-0036-1591876]
[3]
(a)Kuwano, R.; Sato, K.; Kurokawa, T.; Karube, D.; Ito, Y. J. Am. Chem. Soc., 2000, 122, 7614-7615.
[http://dx.doi.org/10.1021/ja001271c]
(b)Wang, D.S.; Chen, Q-A.; Li, W.; Yu, C-B.; Zhou, Y-G.; Zhang, X. J. Am. Chem. Soc., 2010, 132(26), 8909-8911.http://dx.doi.org/
[http://dx.doi.org/10.1021/ja103668q] [PMID: 20552968]
(c)Duan, Y.; Li, L.; Chen, M-W.; Yu, C-B.; Fan, H-J.; Zhou, Y-G. J. Am. Chem. Soc., 2014, 136(21), 7688-7700.http://dx.doi.org/
[http://dx.doi.org/10.1021/ja502020b] [PMID: 24833267]
[4]
(a)Cacchi, S.; Fabrizi, G. Chem. Rev., 2005, 105(7), 2873-2920.
[http://dx.doi.org/10.1021/cr040639b] [PMID: 16011327]
(b)Shiri, M. Chem. Rev., 2012, 112(6), 3508-3549.
[http://dx.doi.org/10.1021/cr2003954] [PMID: 22390139]
(c)Boyarskiy, V.P.; Ryabukhin, D.S.; Bokach, N.A.; Vasilyev, A.V. Chem. Rev., 2016, 116(10), 5894-5986.
[http://dx.doi.org/10.1021/acs.chemrev.5b00514] [PMID: 27111159]
[5]
(a)Bur, S.K.; Padwa, A. Chem. Rev., 2004, 104(5), 2401-2432.
[http://dx.doi.org/10.1021/cr020090l] [PMID: 15137795]
(b)Mąkosza, M.; Wojciechowski, K. Chem. Rev., 2004, 104(5), 2631-2666.
[http://dx.doi.org/10.1021/cr020086+] [PMID: 15137803]
(c)Busto, E.; Gotor-Fernández, V.; Gotor, V. Chem. Rev., 2011, 111(7), 3998-4035.
[http://dx.doi.org/10.1021/cr100287w] [PMID: 21526748]
(d)Zhang, H.; Hu, R-B.; Liu, N.; Li, S-X.; Yang, S-D. Org. Lett., 2016, 18(1), 28-31.
[http://dx.doi.org/10.1021/acs.orglett.56b03053] [PMID: 26673685]
(e)Morimoto, N.; Morioku, K.; Suzuki, H.; Takeuchi, Y.; Nishina, Y. Org. Lett., 2016, 18(9), 2020-2023.
[http://dx.doi.org/10.1021/acs.orglett.6b00629] [PMID: 27119318]
(f)Petrone, D.A.; Kondo, M.; Zeidan, N.; Lautens, M. Chemistry, 2016, 22(16), 5684-5691.
[http://dx.doi.org/10.1002/chem.201600118] [PMID: 26945798]
[6]
(a)Bras, J.L. J. Chem. Rev., 2011, 111, 1170-1214.
(b)Yang, Y.; Lan, J. J. Chem. Rev., 2017, 117, 8787-8863.
[http://dx.doi.org/10.1021/acs.chemrev.6b00567]
[7]
(a)Colby, D.A.; Bergman, R.G.; Ellman, J.A. Chem. Rev., 2010, 110(2), 624-655.
[http://dx.doi.org/10.1021/cr900005n] [PMID: 19438203]
(b)Deb, M.L.; Pegu, C.D.; Deka, B.; Dutta, P.; Kotmale, A.S.; Baruah, P.K. Eur. J. Org. Chem., 2016, 3441-3448.
[http://dx.doi.org/10.1002/ejoc.201600546]
(c)Modi, A.; Ali, W.; Patel, B.K. Adv. Synth. Catal., 2016, 358, 2100-2107.
[http://dx.doi.org/10.1002/ads.201600067]
(d)Pu, F.; Li, Y.; Song, Y-H.; Xiao, J.; Liu, Z-W.; Wang, C.; Liu, Z-T.; Chen, J-G.J. Adv. Synth. Catal., 2016, 358, 539-542.
[http://dx.doi.org/10.1002/adsc.2015600874]
(e)Deb, M.L.; Borpatra, P.J.; Pegu, C.D.; Thakuria, R.; Saikia, P.J.; Baruah, P.K. ChemistrySelect, 2017, 2, 140-146.
[http://dx.doi.org/10.1002/slct.201601857]
(f)Badigenchala, S.; Sekar, G. J. Org. Chem., 2017, 82(14), 7657-7665.
[http://dx.doi.org/10.1021/acs.joc.7b01080] [PMID: 28682077]
[8]
(a)Gritsch, P.J.; Leitner, C.; Pfaffenbach, M.; Gaich, T. Angew. Chem. Int. Ed., 2014, 53, 1208-1217.http://dx.doi.org/
[http://dx.doi.org/10.1002/anie.201307391]
(b)Leitch, J.A.; Bhonoah, Y.; Frost, C.G. ACS Catal., 2017, 7, 5618-5627.
[http://dx.doi.org/10.1021/acscatal.7b01785]
[9]
Jean, L.B.; Jacques, M. Synthesis, 2019, 51, 2871-2890.
[http://dx.doi.org/10.1055/s-0037-1611478]
[10]
(a)Liu, C.; Yuan, J.; Gao, M.; Tang, S.; Li, W.; Shi, R.; Lei, A. Chem. Rev., 2015, 115(22), 12138-12204.
[http://dx.doi.org/10.1021/cr500431s] [PMID: 26558751]
(b)Palmieri, A.; Petrini, M. Synthesis, 2019, 51, 829-841.
[http://dx.doi.org/10.1055/s-0037-1610349]
[11]
Hummel, J.R.; Boerth, J.A.; Ellman, J.A. Chem. Rev., 2017, 117(13), 9163-9227.
[http://dx.doi.org/10.1021/acs.chemrev.6b00661] [PMID: 27936637]
[12]
(a)Trost, B.M.; Gnanamani, E.; Hung, C-I. Angew. Chem. Int. Ed., 2017, 56, 10451-10456.
[http://dx.doi.org/10.1002/anie.201705315]
(b)Bandini, M.; Eichholzer, A.; Tragni, M.; Umani-Ronchi, A. Angew. Chem. Int. Ed., 2008, 47, 3238-3241.
[http://dx.doi.org/10.1002/anie.2001705685]
[13]
(a)Trost, B.M.; Quancard, J. J. Am. Chem. Soc., 2006, 128(19), 6314-6315.
[http://dx.doi.org/10.1021/ja0608139] [PMID: 16683785]
(b)Zaitsev, A.B.; Gruber, S.; Plüss, P.A.; Pregosin, P.S.; Veiros, L.F.; Wörle, M. J. Am. Chem. Soc., 2008, 130(35), 11604-11605.
[http://dx.doi.org/10.1021/ja804379k] [PMID: 18681436]
(c)Liu, W-B.; He, H.; Dai, L-X.; You, S-L. Synthesis, 2009, 2076-2082.
(d)Wu, Q-F.; He, H.; Liu, W-B.; You, S-L. J. Am. Chem. Soc., 2010, 132(33), 11418-11419.
[http://dx.doi.org/10.1021/ja105111n ] [PMID: 20677752]
(e)Hoshi, T.; Sasaki, K.; Sato, S.; Ishii, Y.; Suzuki, T.; Hagiwara, H. Org. Lett., 2011, 13(5), 932-935.
[http://dx.doi.org/10.1021/ol102977b] [PMID: 21261277]
(f)Stanley, L.M.; Hartwig, J.F. Angew. Chem. Int. Ed., 2009, 48, 7841-7844.
[http://dx.doi.org/10.1002/anie.200904338]
[14]
Festa, A.A.; Zalte, R.R.; Golantsov, N.E.; Varlamov, A.V.; Van der Eycken, E.V.; Voskressensky, L.G. J. Org. Chem., 2018, 83(16), 9305-9311.
[http://dx.doi.org/10.1021/acs.joc.8b01279] [PMID: 29944827]
[15]
Chen, J.; Ferreira, A.J.; Beaudry, C.M. Angew. Chem. Int. Ed., 2014, 53, 11931-11934.
[http://dx.doi.org/10.1002/anie.201407336]
[16]
(a)Mann, G.; Hartwig, J.F.; Driver, M.S.; Fernández-Rivas, C. J. Am. Chem. Soc., 1998, 120, 827-828.
[http://dx.doi.org/10.1021/ja973524g]
(b)Antilla, J.C.; Klapars, A.; Buchwald, S.L. J. Am. Chem. Soc., 2002, 124(39), 11684-11688.
[http://dx.doi.org/10.1021/ja027433h ] [PMID: 12296734]
(c)Modha, S.G.; Greaney, M.F. J. Am. Chem. Soc., 2015, 137(4), 1416-1419.
[http://dx.doi.org/10.1021/ja5124754] [PMID: 25588092]
(d)Kong, L.; Sun, Y.; Zheng, Z.; Tang, R.; Wang, M.; Li, Y. Org. Lett., 2018, 20(17), 5251-5255.
[http://dx.doi.org/10.1021/acs.orglett.8b02197] [PMID: 30125113]
[17]
Lorton, C.; Voituriez, A. J. Org. Chem., 2018, 83(10), 5801-5806.
[http://dx.doi.org/10.1021/acs.joc.8b00457] [PMID: 29733208]
[18]
Zhou, X-Y.; Chen, X. Synthesis, 2019, 51, 516-521.
[http://dx.doi.org/10.1055/s-0037-1609937]
[19]
(a)Acharya, C.; Dey, S.; Jaisankar, P. Tetrahedron Lett., 2012, 53, 5548-5551.
[http://dx.doi.org/10.1016/j.tetlet.2012.08.034]
(b)Zedda, G.; Simbula, G.; Begala, M.; Pibiri, M.; Floris, C.; Casu, M.; Casu, L.; Tocco, G. Arch. Pharm. (Weinheim), 2012, 345(3), 195-202.
[http://dx.doi.org/10.1002/ardp.201100104] [PMID: 22715502]

Rights & Permissions Print Cite
Article Metrics
53
1
Wayfinder Image
Open Access Journals Promotions
© 2024 Bentham Science Publishers | Privacy Policy