Citation: Ameri Mohsen, Asghari Alireza, Amoozadeh Ali, Bakherad Mohammad. A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution[J]. Chinese Chemical Letters, ;2017, 28(5): 1031-1034. doi: 10.1016/j.cclet.2016.11.022 shu

A new approach for one-pot, green synthesis of new polycyclic indoles in aqueous solution

a.
Department of Chemistry, Semnan University, Semnan 35195-363, Iran
b.
College of Chemistry, Shahrood University of Technology, Shahrood, Iran

Corresponding author: Asghari Alireza, aasghari@semnan.ac.ir
Received Date: 29 July 2016
Revised Date: 24 October 2016
Accepted Date: 31 October 2016
Available Online: 22 May 2016

Figures(5)

Electro-oxidation of phenylamine derivatives (1a and 1b) have been studied in the presence of pyrazolidine-3,5-dione (3) as a nucleophile in phosphate buffer solution mixed with ethanol, using voltammetric and spectroscopic techniques. The obtained results indicated that the oxidized form of phenylamines (2a and 2b) participate in Michael addition type reactions with pyrazolidine-3,5-dione (3) and via ECECCCCC mechanisms convert to the corresponding new polycyclic indoles (12a and 12b). In the present study, new polycyclic indole derivatives were synthesized with good yields and high purity using a facile, one-pot and environmentally friendly electrochemical method, without any chemical catalysts, toxic solvents and hard conditions.
- Electro-oxidation,
- Phenylamine,
- Polycyclic indoles,
- Environmentally friendly,
- ECECCCCC mechanism
1. [1]
  Sundberg R.. The Chemistry of Indoles[J]. Elsevier, 2012.
2. [2]
  Pelletier S.W.. Alkaloids:Chemical and Biological Perspectives[J]. Springer, 1999.
3. [3]
  Shaheen R.M., Davis D.W., Liu W.. Antiangiogenic therapy targeting the tyrosine kinase receptor for vascular endothelial growth factor receptor inhibits the growth of colon cancer liver metastasis and induces tumor and endothelial cell apoptosis[J]. Cancer Res., 1999,59:5412-5416.
4. [4]
  Vice S.F., Friesen R.W., Dmitrienko G.I.. C-2-side chain modification of 2-methyl-3-alkylindoles via 3-methylthioindolenines:a new approach to pyrrolo[1,2-a] indoles[J]. Tetrahedron Lett., 1985,26:165-168. doi: 10.1016/S0040-4039(00)61870-1
5. [5]
  Weissgerber R.. Indole in coal tar[J]. Chem. Ber., 1910,43:3520-3528. doi: 10.1002/(ISSN)1099-0682
6. [6]
  Ali S., Ali N., Ahmad Dar B., Pradhan V., Farooqui M.. Chemistry and biology of indoles and indazoles:a mini-review[J]. Mini Rev. Med. Chem., 2013,13:1792-1800. doi: 10.2174/1389557511313120009
7. [7]
  Nencki M.. Ueber sulfoharnstoff-oxalsäureäther[J]. Chemische Berichte, 1874,7:779-780.
8. [8]
  Stöckly F.. Zur Kenntniss der Fäulnissprodukte des Gehirns[J]. J. Prakt. Chem., 1881,24:17-24. doi: 10.1002/prac.18810240102
9. [9]
  Asghari A., Ameri M., Radmannia S.. None-catalyst and clean synthesis of symmetric and asymmetric indoles from electrochemical oxidation of 4-aminophenol and p-phenylenediamine in the presence of malononitrile in green media[J]. J. Electroanal. Chem., 2014,733:47-52. doi: 10.1016/j.jelechem.2014.09.015
10. [10]
  Nematollahi D., Hedayatfar V.. Diversity in electrochemical oxidation of dihydroxybenzenes in the presence of 1-methylindole[J]. J. Chem. Sci., 2011,123:709-717. doi: 10.1007/s12039-011-0132-1
11. [11]
  Salehzadeh H., Nematollahi D., Hesari H.. An efficient electrochemical method for the atom economical synthesis of some benzoxazole derivatives[J]. Green Chem., 2013,15:2441-2446. doi: 10.1039/c3gc40954f
12. [12]
  Ameri M., Asghari A., Amoozadeh A., Bakherad M., Nematollahi D.. Green and highly efficient synthesis of new bis-benzofurans via electrochemical methods under ECECCC mechanism[J]. J. Electrochem. Soc., 2014,161:G75-G80. doi: 10.1149/2.0371410jes
13. [13]
  Beiginejad H., Nematollahi D., Varmaghani F., Bayat M.. Efficient factors on the hydrolysis reaction rate of some para-aminophenol derivatives in acidic pHs[J]. J. Electrochem. Soc., 2013,160:H469-H473. doi: 10.1149/2.084308jes
14. [14]
  Beiginejad H., Nematollahi D., Varmaghani F.. Electrochemical oxidation of some aminophenols in various pHs[J]. J. Electrochem. Soc., 2013,160:H41-H46.
15. [15]
  Maleki A., Nematollahi D.. Mechanism diversity in anodic oxidation of N, Ndimethyl-p-phenylenediamine by varying pH[J]. J. Electroanal. Chem., 2013,704:75-79. doi: 10.1016/j.jelechem.2013.06.002
16. [16]
  Metwally S.A., Moneim M.I.A., Elossely Y.A., Awad R.I., Abou-Hadeed K.. Synthesis and crystal structure of some 3,5-pyrazolidinediones[J]. Chem. Heterocycl. Compd., 2010,46:426-437. doi: 10.1007/s10593-010-0527-9
17. [17]
  Ameri M., Asghari A., Amoozadeh A., Bakherad M., Nematollahi D.. Facile and one-pot, electro-organic synthesis of a new bis-quinone by the ECCE mechanism in green media[J]. Chin. Chem. Lett., 2014,25:1607-1610. doi: 10.1016/j.cclet.2014.06.022
18. [18]
  Nematollahi D., Amani A., Tammari E.. Electrosynthesis of symmetric and highly conjugated benzofuran via a unique ECECCC electrochemical mechanism:evidence for predominance of electrochemical oxidation versus intramolecular cyclization[J]. J. Org. Chem., 2007,72:3646-3651. doi: 10.1021/jo062468b
19. [19]
  Ameri M., Asghari A., Amoozadeh A., Bakherad M., Nematollahi D.. An efficient simple, non-catalytic electrosynthesis of new polycyclic benzofuran derivatives[J]. Tetrahedron Lett., 2015,56:2141-2144. doi: 10.1016/j.tetlet.2015.03.049
20. [20]
  Ameri M., Asghari A., Amoozadeh A., Bakherad M.. First electroorganic synthesis based on a metal-and amine-free sonogashira-type coupling reaction with an ECECECE mechanism[J]. J. Electrochem. Soc., 2015,162:G25-G28. doi: 10.1149/2.0961506jes
21. [21]
  Lu Y., Zhao Y., Wang S.. An efficient synthesis of 2-thio-5-amino substituted benzoquinones via KI catalyzed cascade oxidation/michael addition/oxidation starting from hydroquinone[J]. RSC Adv., 2016,6. doi: 10.1039/c5ra26524j
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