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

Marziyeh Saeedi; Maryam Khoshdoun; Salman Taheri; Azim Ziyaei Halimehjani; Aliasghar Mohammadi; Mohammad Reza Halvagar; Vahid Amani

doi:10.1055/a-1492-9229

SynOpen, Table of Contents

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

Authors

Marziyeh Saeedi

^aChemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Maryam Khoshdoun

^aChemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Salman Taheri∗

^aChemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Azim Ziyaei Halimehjani ∗

^bFaculty of Chemistry, Kharazmi University, P. O. Box 15719-14911, 49 Mofateh Street, Tehran, Iran

^cInstitut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, 79104 Freiburg im Breisgau, Germany
Aliasghar Mohammadi

^aChemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Mohammad Reza Halvagar

^aChemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran
Vahid Amani

^dDepartment of Chemistry, Farhangian University, Tehran, Iran

Abstract

All articles of this category

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.

Key words

thioazlactone - nitroketene dithioacetal - bicyclic pyridine - dithiocarbamate - catalyst-free

Full Text

References

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

Supplementary Material

Supporting Information (PDF) (opens in new window)