Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Efficient and Regioselective Synthesis of Phenothiazine via Ferric Citrate Catalyzed C-S/C-N Cross-Coupling

Author(s): Tonmoy Chitta Das, Syed Aziz Imam Quadri and Mazahar Farooqui*

Volume 16, Issue 1, 2019

Page: [16 - 24] Pages: 9

DOI: 10.2174/1570178615666180806114523

Price: $65

Abstract

Efficient C-S and C-N cross-coupling reactions have been developed for regioselective, scalable and environmentally benign synthesis of substituted phenothiazine derivatives. Cross-coupling reactions were demonstrated on various challenging substrates using non-toxic, highly economical, readily available ferric citrate as a catalyst to get desired product with high regioselectivity. Atom economy is the added advantage of this protocol since additional N-protection step before coupling and eventual deprotection of the same to obtain the desired product arenot required. To the best of our knowledge, this is the first report on the use of inexpensive ferric citrate as a catalyst without involving any ligand for the synthesis of regioselectively substituted phenothiazine.

Keywords: C-N coupling, eco-efficient, ferric citrate catalyst, regioselective, phenothiazine, synthesis.

Graphical Abstract
[1]
(a) Muci, A.R.; Buchwald, S.L. Top. Curr. Chem., 2002, 219, 131.
Meijere, de A.; Diederich, F. Metal-catalyzed cross-coupling reactions; Wiley-VCH: Weinheim, 2004.
(c) Nasr-Esfahani, M.; Hoseini, J.S.; Montazerozohori, M.; Mehrabi, R.; Nasrabadi, H. J. Mol. Catal. Chem., 2014, 382, 99-105.
(d) Pamuk, H.; Aday, B.; Sen, F.; Kaya, M. RSC Adv, 2015, 5, 49295-49300.
(e) Esirden, I.; Erken, E.; Kaya, M.; Sen, F. Catal. Sci. Technol., 2015, 5, 4452-4457.
(f) Erken, E.; Esirden, I.; Kaya, M.; Sen, F. RSC Adv, 2015, 5, 68558-68564.
(g) Sen, B.; Lolak, N.; Parali, O.; Koca, M.; Savk, A.; Akocak, S.; Sen, F. Nano-Structures & Nano-Objects, 2017, 12, 33-40.
(h) Demirci, T.; Celik, B.; Yildiz, Y.; Eris, S.; Sen, F.; Kilbas, B. RSC Adv, 2016, 6, 76948-76956.
(i)Ulus, R.; Yidiz, Y.; Eris, S.; Aday, B.; Sen, F. Chem. Select, 2016, 1, 3861-3865.
(j)Aday, B.; Pamuk, H.; Kaya, M.; Sen, F. J. Nanosci. Nanotechnol., 2016, 16, 6498-6504.
(k)Pamuk, H.; Aday, B.; Sen, F.; Kaya, M. RSC Adv, 2015, 5, 49295-49300.
(l)Aday, B.; Yildiz, Y.; Ulus, R.; Eris, S.; Sen, F.; Kaya, M. New J. Chem., 2016, 40, 748-754.
[2]
(a) Yang, C.T.; Fu, Y.; Huang, Y.B.; Yi, J.; Guo, Q.X.; Lui, L. Angew. Chem., 2009, 48, 7398-7401.
(b) Huang, Y.B. Yang. C.T.; Yi, J.; Deng, X.J.; Fu, Y.; Lui, L. J. Org. Chem., 2011, 76, 800-810.
[3]
Ding, X.; Huang, M.; Yi, Z.; Du, D.; Zhu, X.; Wan, Y. J. Org. Chem., 2017, 82, 5416-5423.
[4]
Dahl, T.; Tornoe, C.W.; Bang-Andersen, B.; Nielsen, P.; Jorgensen, M. Angew. Chem. Int. Ed., 2008, 47, 1726-1728.
[5]
(a) Bolm, C.; Legros, J.; Paih, J.L.; Zani, L. Chem. Rev., 2004, 104, 6217-6254.
(b) Damodara, D.; Arundhati, R.; Likhar, P.R. Catal. Sci. Technol., 2013, 3, 797-802.
(c) Bristi, O.; Correa, A.; Bolm, C. Angew. Chem., 2008, 120, 596-598.
(d) Sun, C.L.; Li, B.J.; Shi, Z.J. Chem. Rev., 2011, 111, 1293-1314.
(e) Wang, H.B.; Wang, L.; Shang, J.S.; Li, X.; Wang, H.Y.; Gui, J.; Lei, A.W. Chem. Commun., 2012, 48, 76-78.
(f) Gopalaiah, K. Chem. Rev., 2013, 113, 3248-3296.
(g) Correa, A.; Carril, M.; Bolm, C. Angew. Chem., 2007, 119, 9018-9021.
(h) Buchwald, S.L.; Bolm, C. Angew. Chem. Int. Ed., 2009, 48, 5586-5587.
[6]
(a) Basta-Kaim, A.; Budziszewska, B.; Jaworska-Feil, L.; Tetich, M.; Kubera, M.; Leskiewicz, M.; Otczyk, M.; Lason, W. Neuropsycopharmalogy, 2006, 31, 853-865.
[7]
(a) Sudeshna, G.; Parimal, K. Eur. J. Pharmacol., 2010, 648, 6-14.
(b) Motohashi, N.; Kawase, M.; Satoh, K.; Sakagami, H. Curr. Drug Targets, 2006, 7, 1055-1066.
[8]
Ohlow, M.J.; Moosmann, B. Drug Discov. Today, 2011, 16, 119-131.
[9]
Jaszczyszyn, A.; Gasiorowski, K.; Swiatek, P.; Malinka, W.; Cieslik-Boczula, K.; Petrus, J.; Czarnik-Matusewicz, B. Pharmacol. Rep., 2012, 64, 16-23.
[10]
Gutierrez, A.; Pan, L.; Groen, W.J.R.; Baleydier, F.; Kentsis, A.; Marineau, J.; Grebliunaite, R.; Kozakewich, E.; Reed, C.; Pflumio, F.; Poglio, S.; Uzan, B.; Clemons, P.; VerPlank, L.; An, F.; Burbank, J.; Norton, S.; Tolliday, N.; Steen, H.; Weng, P.A.; Yuan, H.; Bradner, E.J.; Mitsiades, C.; Look, T.A.; Aster, C.J. J. Clin. Invest., 2014, 124, 644-655.
[11]
Belei, D.; Dumea, C.; Samson, A.; Farce, A.; Dubois, J.; Bicu, E.; Ghinet, A. Bioorg. Med. Chem. Lett., 2012, 22, 4517-4522.
[12]
Mayer, M.; Lang, T.; Gerber, S.; Madrid, P.B.; Pinto, I.G.; Guy, R.K.; James, T.L. Chem. Biol., 2006, 13, 993-1000.
[13]
(a) Sadanandam, Y.S.; Shetty, M.M.; Rao, A.B.; Rambabu, Y. Eur. J. Med. Chem., 2009, 44, 197-202.
(b) Maddila, S.; Gorle, S.; Singh, M.; Lavanya, P.; Jonnalagadda, S.B. Lett. Drug Des. Discov., 2013, 10, 977-983.
[14]
(a) Kurihara, T.; Motohashi, N.; Sakagami, H.; Molnar, H.J. Anticancer Res., 1999, 19, 4081-4083.
(b) Kurihara, T.; Nojima, K.; Sakagami, H.; Motohashi, N.; Molnar, H. J. Anticancer Res., 1999, 19, 3895-3899.
[15]
Mosnaim, A.; Ranade, V.; Wolf, M.; Puente, J.; Valenzuela, M. Am. J. Ther., 2006, 13, 261-273.
[16]
Madrid, P.B.; Polgar, W.E.; Toll, L.; Tanga, M.J. Bioorg. Med. Chem. Lett., 2007, 17, 3014-3017.
[17]
Archana, P.; Rani, K.; Bajaj, V.K.; Srivastava, R.; Chandra, A. Arzneimittelforschung, 2003, 53, 301-306.
[18]
Tandon, K.V.; Maurya, H.K.; Tripathi, A.; Shiva Keshava, G.B.; Shukla, P.K. Eur. J. Med. Chem., 2009, 44, 1086-1092.
[19]
Lu, W.; Achour, A.; Arlie, M.; Cao, Li.; Andrieu, J-M. J. Immunol., 2001, 167, 2929-2935.
[20]
(a) Yale, H.L. J. Am. Chem. Soc., 1955, 77, 2270-2272.
(b) Sharma, N.; Gupta, R.; Kumar, M.; Gupta, R.R.J. Fluorine Chem., 1999, 98, 153-157.
[21]
(a) Hauck, M.; Schnhaber, J.; Zucchero, A.J.; Hardcastle, K.I.; Mller, T.J.J.; Bunz, U.H.F. J. Org. Chem., 2007, 72, 6714-6725.
(b) Sailer, M.; Franz, A.W.; Mller, T.J.J. Chem. Eur. J.,, 2008, 14, 2602-2614.
(c) Lai, R.Y.; Kong, X.; Jenekhe, S.A.; Bard, A.J. J. Am. Chem. Soc., 2003, 125, 12631-12639.
[22]
Dai, C.; Sun, X.; Tu, X.; Wu, L.; Zhan, D.; Zeng, Q.L. Chem. Commun., 2012, 48, 5367-5369.
[23]
Thome, I.; Bolm, C. Org. Lett., 2012, 14, 1892-1895.
[24]
(a) Smith, N.L. J. Org. Chem., 1950, 15, 1125-1130.
(b) Madrid, P.B.; Polgar, W.E.; Toll, L.; Tanga, M.J. Bioorg. Med. Chem. Lett., 2007, 17, 3014-3017.
[25]
Ma, D.; Geng, Q.; Zhang, H.; Jiang, Y. Angew. Chem. Int. Ed., 2010, 49, 1291-1294.
[26]
Hu, W.; Zhang, S. J. Org. Chem., 2015, 80, 6128-6132.
[27]
Zhou, Y.; Zeng, Q.; Zhang, L. Synth. Commun., 2017, 47, 710-715.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy