Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

12 Issues per year


IMPACT FACTOR 2017: 0.757

CiteScore 2017: 0.68

SCImago Journal Rank (SJR) 2017: 0.277
Source Normalized Impact per Paper (SNIP) 2017: 0.394

Online
ISSN
1865-7117
See all formats and pricing
More options …
Volume 73, Issue 5

Issues

A highly effective and mild protocol for the production of 1-thioamidoalkyl-2-naphthols using 1,3-disulfonic acid imidazolium trifluoroacetate as a dual-functional catalyst

Mostafa Karami / Abdolkarim Zare
Published Online: 2018-04-24 | DOI: https://doi.org/10.1515/znb-2018-0001

Abstract

A solvent-free protocol for the production of 1-thioamidoalkyl-2-naphthols via a one-pot multi-component reaction of arylaldehydes with 2-naphthol and thioacetamide using the ionic liquid 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]) is described. Furthermore, a plausible and attractive mechanism based on the dual functionality of the catalyst is proposed. Because of the dual functionality of [Dsim][TFA] (possessing acidic and basic sites), it is found to be generally highly effective, affording the products in high yields and short reaction times under mild conditions. We claim that this is one of the best protocols for the synthesis of 1-thioamidoalkyl-2-naphthols (in terms of yield, temperature, conditions, and/or the reaction time).

This article offers supplementary material which is provided at the end of the article.

Keywords: 1-thioamidoalkyl-2-naphthol; 1,3-disulfonic acid imidazolium trifluoroacetate ([Dsim][TFA]); dual-functional catalyst; ionic liquid; multi-component reaction; solvent-free reaction

References

  • [1]

    H.-X. Wei, D. Lu, V. Sun, J. Zhang, Y. Gu, P. Osenkowski, W. Ye, D. J. Selkoe, M. S. Wolfe, C. E. Augelli-Szafran, Bioorg. Med. Chem. Lett. 2016, 26, 2133.CrossrefGoogle Scholar

  • [2]

    M. Kidwai, R. Chauhan, Asian J. Org. Chem. 2013, 2, 395.CrossrefGoogle Scholar

  • [3]

    N. Gyemant, H. Engi, Z. Schelz, I. Szatmari, D. Toth, F. Fulop, J. M. Nar, P. D. Witte, Br. J. Cancer 2010, 103, 178.CrossrefGoogle Scholar

  • [4]

    A. Y. Shen, C. T. Tsai, C. L. Chen, Eur. J. Med. Chem. 1999, 34, 877.CrossrefGoogle Scholar

  • [5]

    M. Akaiwa, T. Kanbara, H. Fukumoto, T. Yamamoto, J. Organomet. Chem. 2005, 690, 4192.CrossrefGoogle Scholar

  • [6]

    F. Arnaud-Neu, G. Barrett, D. Corry, S. Cremin, G. Ferguson, J. F. Gallagher, S. J. Harris, M. A. McKervey, M.-J. Schwing-Weill, J. Chem. Soc., Perkin Trans. 1997, 2, 575.Google Scholar

  • [7]

    J. H. Miwa, A. K. Patel, N. Vivatrat, S. M. Popek, A. M. Meyer, Org. Lett. 2001, 3, 3373.CrossrefGoogle Scholar

  • [8]

    J. M. Goldberg, R. F. Wissner, A. M. Klein, E. J. Petersson, Chem. Commun. 2012, 48, 1550.CrossrefGoogle Scholar

  • [9]

    F. Wang, R. Langley, G. Gulten, L. G. Dover, G. S. Besra, W. R. Jacobs Jr., J. C. Sacchettini, J. Exp. Med. 2007, 204, 73.CrossrefGoogle Scholar

  • [10]

    P. W. Tan, A. M. Mak, M. B. Sullivan, D. J. Dixon, J. Seayad, Angew. Chem. Int. Ed. 2017, 56, 16550.CrossrefGoogle Scholar

  • [11]

    Y. Singjunla, M. Pigeaux, R. Laporte, J. Baudoux, J. Rouden, Eur. J. Org. Chem. 2017, 2017, 4319.CrossrefGoogle Scholar

  • [12]

    M. N. Xanthopoulou, S. K. Hadjikakou, N. Hadjiliadis, E. R. Milaeva, J. A. Gracheva, V. Y. Tyurin, N. Kourkoumelis, K. C. Christoforidis, A. K. Metsios, S. Karkabounas, K. Charalabopoulos, Eur. J. Med. Chem. 2008, 43, 327.CrossrefGoogle Scholar

  • [13]

    C. Jiang, P. J. Young, S. Brown-Xu, J. C. Gallucci, M. H. Chisholm, Inorg. Chem. 2017, 56, 1433.CrossrefGoogle Scholar

  • [14]

    A. Khazaei, F. Abbasi, A. R. Moosavi-Zare, M. Khazaei, M. H. Beyzavi, J. Chin. Chem. Soc. 2015, 62, 850.CrossrefGoogle Scholar

  • [15]

    H. Eshghi, G. H. Zohuri, S. Damavandi, Synth. Commun. 2012, 42, 516.CrossrefGoogle Scholar

  • [16]

    A. Ghorbani-Choghamarani, S. Rashidimoghadam, Res. Chem. Intermed. 2015, 41, 6271.CrossrefGoogle Scholar

  • [17]

    A. Khazaei, M. A. Zolfigol, A. R. Moosavi-Zare, F. Abi, A. Zare, H. Kaveh, V. Khakyzadeh, M. Kazem-Rostami, A. Parhami, H. Torabi-Monfared, Tetrahedron 2013, 69, 212.CrossrefGoogle Scholar

  • [18]

    A. Khazaei, F. Abbasi, A. R. Moosavi-Zare, J. Sulfur Chem. 2015, 36, 364.CrossrefGoogle Scholar

  • [19]

    A. Zare, H. Kaveh, M. Merajoddin, A. R. Moosavi-Zare, A. Hasaninejad, M. A. Zolfigol, Phosphorus Sulfur Silicon Relat. Elem. 2013, 188, 573.CrossrefGoogle Scholar

  • [20]

    A. Hassanabadi, M. R. Hosseini-Tabatabaei, J. Chem. Res. 2012, 36, 510.CrossrefGoogle Scholar

  • [21]

    A. Zare, S. Akbarzadeh, E. Foroozani, H. Kaveh, A. R. Moosavi-Zare, A. Hasaninejad, M. Mokhlesi, M. H. Beyzavi, M. A. Zolfigol, J. Sulfur Chem. 2012, 33, 259.CrossrefGoogle Scholar

  • [22]

    A. S. Amarasekara, Chem. Rev. 2016, 116, 6133.CrossrefGoogle Scholar

  • [23]

    R. L. Vekariya, J. Mol. Liq. 2017, 227, 44.CrossrefGoogle Scholar

  • [24]

    A. A. Marzouk, A. A. Abdelhamid, S. K. Mohamed, J. Simpson, Z. Naturforsch. 2017, 72b, 23.Google Scholar

  • [25]

    A. K. Dutta, P. Gogoi, R. Borah, RSC Adv. 2014, 4, 41287.CrossrefGoogle Scholar

  • [26]

    M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, H. G. Kruger, Z. Asgari, V. Khakyzadeh, M. Kazem-Rostami, J. Org. Chem. 2012, 77, 3640.CrossrefGoogle Scholar

  • [27]

    A. Zare, Z. Nasouri, J. Mol. Liq. 2016, 216, 364.CrossrefGoogle Scholar

  • [28]

    A. Zare, T. Yousofi, A. R. Moosavi-Zare, RSC Adv. 2012, 2, 7988.CrossrefGoogle Scholar

  • [29]

    M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Appl. Catal. A 2011, 400, 70.CrossrefGoogle Scholar

  • [30]

    A. R. Moosavi-Zare, M. A. Zolfigol, V. Khakyzadeh, C. Böttcher, M. H. Beyzavi, A. Zare, A. Hasaninejad, R. Luque, J. Mater. Chem. A 2014, 2, 770.CrossrefGoogle Scholar

  • [31]

    J. Safaei-Ghomi, S. H. Nazemzadeh, H. Shahbazi-Alavi, Z. Naturforsch. 2017, 72b, 927.Google Scholar

  • [32]

    E. Lamera, S. Bouacida, M. L. Borgne, Z. Bouaziz, A. Bouraiou, Tetrahedron Lett. 2017, 58, 1305.CrossrefGoogle Scholar

  • [33]

    M. Himaja, D. Poppy, K. Asif, Int. J. Res. Ayurveda Pharm. 2011, 2, 1079.Google Scholar

  • [34]

    G. B. D. Rao, S. Nagakalyanb, G. K. Prasad, RSC Adv. 2017, 7, 3611.CrossrefGoogle Scholar

  • [35]

    A. Zare, A. R. Moosavi-Zare, M. Merajoddin, M. A. Zolfigol, T. Hekmat-Zadeh, A. Hasaninejad, A. Khazaei, M. Mokhlesi, V. Khakyzadeh, F. Derakhshan-Panah, M. H. Beyzavi, E. Rostami, A. Arghoon, R. Roohandeh, J. Mol. Liq. 2012, 167, 69.CrossrefGoogle Scholar

About the article

Received: 2018-01-01

Accepted: 2018-02-26

Published Online: 2018-04-24

Published in Print: 2018-05-24


Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 5, Pages 289–293, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2018-0001.

Export Citation

©2018 Walter de Gruyter GmbH, Berlin/Boston.Get Permission

Supplementary Article Materials

Comments (0)

Please log in or register to comment.
Log in