CC BY-NC-ND 4.0 · SynOpen 2021; 05(02): 108-113
DOI: 10.1055/a-1492-9229
paper
Virtual Collection in Honor of Prof. Issa Yavari

Synthesis of Functionalized Bicyclic Pyridones Containing the Dithiocarbamate Group Using Thioazlactones, Diamines, and Nitroketene Dithioacetal

Marziyeh Saeedi
a   Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Maryam Khoshdoun
a   Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Salman Taheri
a   Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
b   Faculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran
c   Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104 Freiburg im Breisgau, Germany
,
Aliasghar Mohammadi
a   Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Mohammad Reza Halvagar
a   Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
,
Vahid Amani
d   Department of Chemistry, Farhangian University, Tehran, Iran
› Author Affiliations
We thank the Research Council of the Chemistry and Chemical Engineering Research Center of Iran (CCERCI) and the Faculty of Chemistry of Kharazmi University for supporting this work. A.Z.H. thanks the Alexander von Humboldt-Stiftung for supporting his research in the Albert-Ludwigs-Universität Freiburg.


Abstract

An efficient method for the synthesis of highly substituted bicyclic pyridone derivatives containing the dithiocarbamate group is reported via a one-pot three-component reaction of 2-(alkylthio)thio­azlactones, diamines, and nitroketene dithioacetal in EtOH under catalyst-free conditions. The reaction proceeds via a domino amidation–­intramolecular 1,4-addition-type Friedel–Crafts alkylation reaction to afford the corresponding fused bicyclic pyridones with high yields and diastereoselectivity.

Supporting Information



Publication History

Received: 19 March 2021

Accepted after revision: 26 April 2021

Accepted Manuscript online:
27 April 2021

Article published online:
11 May 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
  • References

    • 1a Taguchi H, Yazawa H, Arnett JF, Kishi Y. Tetrahedron Lett. 1977; 7: 627
    • 1b Shen W, Coburn CA, Bornmann WG, Danishefsky S. J. Org. Chem. 1993; 58: 611
    • 1c Paulvannan K, Stille JR. J. Org. Chem. 1994; 59: 1613
    • 1d Aaberg V, Almqvist F. Org. Biomol. Chem. 2007; 5: 1827
    • 1e Pinkner JS, Remaut H, Miller E, Aaberg V, Pemberton N, Hedenstroem M, Larsson A, Seed P, Waksman G, Hultgren SJ, Almqvist F. Proc. Natl. Acad. Sci. U.S.A. 2006; 103: 17897
    • 1f Marcaurelle LA, Johannes C, Yohannes D, Tillotson BP, Mann D. Bioorg. Med. Chem. Lett. 2009; 19: 2500
  • 2 Yin L, Hu Q.-Z, Hartmann LW. J. Med. Chem. 2013; 56: 460
  • 3 Collins I, Moyes C, Davey WB, Rowley M, Bromidge FA, Quirk K, Atack JR, McKernan RM, Thompson SA, Wafford K, Dawson GR, Pike A, Sohal B, Tsou NN, Ball RG, Castro JL. J. Med. Chem. 2002; 45: 1887
    • 4a Fan X, Feng D, Qu Y, Zhang X, Wang J, Loiseau PM, Andrei G, Snoeck R, De Clercq E. Bioorg. Med. Chem. Lett. 2010; 20: 809
    • 4b Hussain H, Al-Harrasi A, Al-Rawahi A, Green IR, Gissons S. Chem. Rev. 2014; 114: 10369
  • 5 Flamm RK, Vojtko C, Chu DT. W, Beyer QL. J, Hensey D, Ramer N, Clement JJ, Tanaka SK. Antimicrob. Agents Chemother. 1995; 4: 964
  • 6 Haga A, Tamoto H, Ishino M, Kimura E, Sugita T, Kinoshita K, Takahashi K, Shiro M, Koyama K. J. Nat. Prod. 2013; 76: 750
  • 7 Jones ED, Vandegraaff N, Le G, Choi N, Issa W, Macfarlane K, Thienthong N, Winfield LJ, Coates JA. V, Lu L, Li X.-M, Feng B, Yu C.-J, Rhodes DI, Deadman JJ. Bioorg. Med. Chem. Lett. 2010; 20: 5913
  • 8 Amr AG, Abdulla MM. Bioorg. Med. Chem. 2006; 14: 4341
    • 9a Zhao M.-X, Wang M.-X, Huang Z.-T. Tetrahedron 2002; 58: 1309
    • 9b Kubo K, Ito N, Souzu I, Isomura Y, Homma H, Murakami M. US4284778A, 1981
    • 9c Hehemann DG, Winnik W. J. Heterocycl. Chem. 1994; 31: 393
    • 9d Liao W.-L, Li S.-Q, Wang J, Zhang Z.-Y, Yang Z.-W, Xu D, Xu C, Lan H.-T, Chen Z.-Z, Xu Z.-G. ACS Comb. Sci. 2016; 18: 65
    • 9e Kavala V, Wang CC, Wang YH, Kuo CW, Janreddy D, Huang WC, Kuo TS, He CH, Chen ML, Yao CF. Adv. Synth. Catal. 2014; 356: 2609
    • 9f Lu J, Gong X, Yang H, Fu H. Chem. Commun. 2010; 46: 4172
    • 9g Sunke R, Adepu R, Kapavarapu R, Chintala S, Meda CL. T, Parsa KV. L, Pal M. Chem. Commun. 2013; 49: 3570
  • 10 Huang Z.-T, Liu Z.-R. Heterocycles 1986; 24: 2247
  • 11 Huang Z.-T, Tzai LH. Chem. Ber. 1986; 2208
  • 12 Yan S.-J, Niu Y.-F, Huang R, Lin J. Synlett 2009; 2821
  • 13 Yao C, Jiao W, Xiao Z, Xie Y, Li T, Wang X, Liu R, Yu C. RSC Adv. 2013; 3: 10801
  • 14 Chen X, Zhu D, Wang X, Yan S, Lin J. Tetrahedron 2013; 69: 9224
  • 15 Ren L, Lou Y, Chen N, Xia S, Shao X, Xu X, Li Z. Synth. Commun. 2014; 44: 858
    • 16a Zhao M.-X, Wang M.-X, Huang Z.-T. Tetrahedron 2002; 58: 1309
    • 16b Meyer H. Liebigs Ann. Chem. 1981; 9: 1523
    • 16c Takahashi M, Nozaki C, Shibazaki Y. Chem. Lett. 1987; 6: 1229
    • 16d Raymond CF. J, Pravin P. Tetrahedron 1998; 54: 6191
    • 16e Charkrabarti S, Panda K, Misra NC, Ila H, Junjappa H. Synlett 2005; 1437
    • 16f Yu CY, Yang PH, Zhao MX, Huang ZT. Synlett 2006; 1835
    • 16g Sukach VA, Bolbut AV, Petin AY, Vovk MV. Synthesis 2007; 835
    • 17a Kanchi S, Singh P, Bisetty K. Arab. J. Chem. 2014; 7: 11
    • 17b Hussein MA, El-Shorbagi A.-N, Khallil A.-R. Arch. Pharm. Med. Chem. 2001; 334: 305
    • 17c Eng G, Song X, Duong Q, Strickman D, Glass J, May L. Appl. Organomet. Chem. 2003; 17: 218
    • 18a Kiran Kumar ST. V. S, Kumar L, Sharma VL, Jain A, Jain RK, Maikhuri JP, Kumar M, Shukla PK, Gupta G. J. Med. Chem. 2008; 43: 2247
    • 18b Kumar L, Lal N, Kumar V, Sarswat A, Jangir S, Bala V, Kumar L, Kushwaha B, Pandey AK, Siddiqi MI, Shukla PK, Maikhuri JP, Gupta G, Sharma VL. Eur. J. Med. Chem. 2013; 70: 68
    • 18c Tripathi RP, Khan AR, Setty BS, Bhaduri AP. Acta Pharm. 1996; 46: 169
    • 18d Ates O, Kocabalkanli A, Cesur N, Otuk G. Farmaco 1998; 53: 541
    • 18e Nofal ZM, Fahmy HH, Mohamed HS. Arch. Pharm. Res. 2002; 25: 28
    • 18f Singh N, Gupta S, Nath G. Appl. Organomet. Chem. 2000; 14: 484
    • 19a Cheng Y, Yang H.-B, Huang Z.-T, Wang M.-X. Tetrahedron Lett. 2001; 42: 1757
    • 19b Nazarenko KG, Shvidenko KV, Pinchuk AM, Tolmachev AA. Monatsh. Chem. 2005; 136: 211
    • 19c Zhou A, Pittman CU. Tetrahedron Lett. 2006; 46: 2045
    • 19d Huang Z.-T, Wang M.-X. Heterocycles 1994; 37: 1233
    • 19e Yan S.-J, Chen Y.-L, Liu L, He N.-Q, Lin J. Green Chem. 2010; 12: 2043
    • 19f Yu F.-C, Huang R, Ni H.-C, Fan J, Yan S.-J, Lin J. Green Chem. 2013; 15: 453
    • 19g Wen L.-R, Li Z.-R, Li M, Cao H. Green Chem. 2012; 14: 707
    • 19h Li M, Shao P, Wang S.-W, Kong W, Wen L.-R. J. Org. Chem. 2012; 77: 8956
    • 19i Yu F.-C, Yan S.-J, Hu L, Wang Y.-C, Lin J. Org. Lett. 2011; 13: 4782
    • 19j Wen L.-R, Liu C, Li M, Wang L.-J. J. Org. Chem. 2010; 75: 7605
    • 20a Cui B.-D, Zuo J, Zhao J.-Q, Zhou M.-Q, Wu Z.-J, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2014; 79: 5305
    • 20b Matiadis D, Igglessi-Markopoulou O, McKee V, Markopoulos J. Tetrahedron 2014; 70: 2439
    • 20c Conway PA, Devine K, Paradisi F. Tetrahedron 2009; 65: 2935
    • 20d Sun W, Zhu G, Wu C, Li G, Hong L, Wang R. Angew. Chem. Int. Ed. 2013; 52: 8633
    • 20e Cui B.-D, Zuo J, Zhao J.-Q, Zhou M.-Q, Wu Z.-J, Zhang X.-M, Yuan W.-C. J. Org. Chem. 2014; 79: 5305
    • 20f Melhado AD, Amarante GW, Wang ZJ, Luparia M, Toste FD. J. Am. Chem. Soc. 2011; 133: 3517
    • 20g Rodríguez-Docampo Z, Quigley C, Tallon S, Connon SJ. J. Org. Chem. 2012; 77: 2407
    • 20h Trost BM, Czabaniuk LC. J. Am. Chem. Soc. 2012; 134: 5778
    • 21a Bernabe M, Cuevas O, Fernandez-Alvarez E. Synthesis 1977; 191
    • 21b Arenal I, Bernabe M, Cuevas O, Fernandez-Alvarez E. Tetrahedron 1983; 39: 1387
    • 21c Bernabe M, Cuevas O, Fernandez-Alvarez E. Eur. J. Med. Chem. 1979; 14: 33
    • 21d Bernabe M, Cuevas O, Fernandez-Alvarez E. Tetrahedron Lett. 1977; 18: 895
  • 22 Ziyaei Halimehjani A, Khoshdoun M. J. Org. Chem. 2016; 81: 5699
    • 23a Ziyaei Halimehjani A, Hosseinkhany S. Synthesis 2015; 47: 3147
    • 23b Ziyaei Halimehjani A, Alaei MA, Soleymani Movahed F, Jomeh N, Saidi MR. J. Sulf. Chem. 2016; 37: 529
    • 23c Schlüter T, Ziyaei Halimehjani A, Wachtendorf D, Schmidtmann M, Martens J. ACS Comb. Sci. 2016; 18: 456
    • 23d Ziyaei Halimehjani A, Hasani L, Alaei MA, Saidi MR. Tetrahedron Lett. 2016; 57: 883
    • 23e Ziyaei Halimehjani A, Hajiloo Shayegan M, Hashemi MM, Notash B. Org. Lett. 2012; 14: 3838
    • 23f Ziyaei Halimehjani A, Martens J, Schluter T. Tetrahedron 2016; 72: 3958
  • 24 CCDC 1570967 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures.
  • 25 Zhao MX, Wang MX, Huang ZT. Tetrahedron 2002; 58: 1309