Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2016; 48(21): 3785-3793
DOI: 10.1055/s-0035-1561472
DOI: 10.1055/s-0035-1561472
paper
N-Bromosuccinimide-Mediated Synthesis of Substituted Quinoxalines
Further Information
Publication History
Received: 25 March 2016
Accepted after revision: 13 May 2016
Publication Date:
24 June 2016 (online)
Abstract
An efficient and simple N-bromosuccinimide-mediated two-step synthesis of substituted quinoxalines from 1,2-diarylacetylenes and 1,2-diaminobenzenes in boiling AcOH, during a one-pot procedure has been developed. All the structures of the substituted quinoxalines were confirmed, some by single-crystal X-ray crystallography. Possible reaction pathways were discussed, and some data were matched with the previous work.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561472.
- Supporting Information
-
References
- 1a Sessler JL, Maeda H, Mizuno T, Lynch VM, Furuta H. J. Am. Chem. Soc. 2002; 124: 13474
- 1b Castro PP, Zhao G, Masangkay GA, Hernandez C, Gutierrez-Tunstad LM. Org. Lett. 2004; 6: 333
- 2 Song HJ, Lee TH, Han MH, Lee JY, Moon DK. Polymer 2013; 54: 1072
- 3a Liu XM, Zhao Q, Li Y, Song WC, Li YP, Chang Z, Bu XH. Chin. Chem. Lett. 2013; 24: 962
- 3b Shi J, Chai Z, Su J, Chen J, Tang R, Fan K, Zhang L, Han H, Qin J, Peng T, Li Q, Li Z. Dyes Pigments 2013; 98: 405
- 3c Li H, Koh TM, Hagfeldt A, Gratzel M, Mhaisalkar SG, Grimsdale AC. Chem. Commun. 2013; 49: 2409
- 3d Venkateswararao A, Tyagi P, Thomas KR. J, Chen PW, Ho KC. Tetrahedron 2014; 70: 6318
- 4 Kotharkar SA, Shinde DB. Bioorg. Med. Chem. Lett. 2006; 16: 6181
- 5 Rodrigues FA. R, da S Bomfim I, Cavalcanti BC, do Ó Pessoa C, Wardell JL, Wardell SM. S. V, Pinheiro AC, Kaiser CR, Nogueira TC. M, Low JN, Gomes LR, de Souza MV. N. Bioorg. Med. Chem. Lett. 2014; 24: 934
- 6 Hui X, Desrivot J, Bories C, Loiseau PM, Franck X, Hocquemiller R, Figadere B. Bioorg. Med. Chem. Lett. 2006; 16: 815
- 7 Parhi AK, Zhang Y, Saionz KW, Pradhan P, Kaul M, Trivedi K, Pilch DS, LaVoie EJ. Bioorg. Med. Chem. Lett. 2013; 23: 4968
- 8 Guillon J, Moreau S, Mouray E, Sinou V, Forfar I, Fabre SB, Desplat V, Millet P, Parzy D, Jarry C, Grellier P. Bioorg. Med. Chem. 2008; 16: 9133
- 9 Guillon J, Forfar I, Mamani-Matsuda M, Desplat V, Saliege M, Thiolat D, Massip S, Tabourier A, Leger J.-M, Dufaure B, Haumont G, Jarry C, Mossalayi D. Bioorg. Med. Chem. 2007; 15: 194
- 10 For aldehydes, see: Zhang C, Xu Z, Zhang L, Jiao N. Tetrahedron 2012; 68: 5258
- 11a Cho CS, Ren WX, Shim SC. Tetrahedron Lett. 2007; 48: 4665
- 11b Robin RS, Taylor RJ. K. Synlett 2005; 1003
- 11c Meshram HM, Ramesh P, Kumar GS, Reddy BC. Tetrahedron Lett. 2010; 51: 4313
- 11d Chang MY, Lee TW, Hsu RT, Yen TL. Synthesis 2011; 3143
- 11e Kim SY, Park KH, Chung YK. Chem. Commun. 2005; 1321
- 11f Pan F, Chen TM, Cao JJ, Zou JP, Zhang W. Tetrahedron Lett. 2012; 53: 2508
- 11g Meshram HM, Kumar GS, Ramesh P, Reddy BC. Tetrahedron Lett. 2010; 51: 2508
- 11h Qi C, Jiang H, Huang L, Chen Z, Chen H. Synthesis 2011; 387
- 11i Akkilagunta VK, Reddy VP, Kakulapati RR. Synlett 2010; 2571
- 12a Tingoli M, Mazzella M, Panunzi B, Tuzi A. Eur. J. Org. Chem. 2011; 399
- 12b Yang Y, Zhang S, Wu B, Ma M, Chen X, Qin X, He M, Hussain S, Jing C, Ma B, Zhu C. ChemMedChem 2012; 7: 823
- 12c Schmidt B, Krehl S, Hauke S. J. Org. Chem. 2013; 78: 5427
- 12d Huang T.-Q, Qu W.-Y, Ding J.-C, Liu M.-C, Wu H.-Y, Chen J.-X. J. Heterocycl. Chem. 2013; 50: 293
- 12e Edayadulla N, Lee YR. RSC Adv. 2014; 4: 11459
- 12f Dandia A, Parewa V, Maheshwari S, Rathore KS. J. Mol. Catal. A: Chem. 2014; 394: 244
- 12g Xie C, Zhang Z, Yang B, Song G, Gao H, Wen L, Ma C. Tetrahedron 2015; 71: 1831
- 12h Go A, Lee G, Kim J, Bae S, Lee BM, Kim BH. Tetrahedron 2015; 71: 1215
- 13a Antoniotti S, Dunach E. Tetrahedron Lett. 2002; 43: 3971
- 13b Nasar MK, Kumar RR, Perumal S. Tetrahedron Lett. 2007; 48: 2155
- 14a Cho CS, Oh SG. Tetrahedron Lett. 2006; 47: 5633
- 14b You L, Cho EJ, Leavitt J, Ma L.-C, Montelione GT, Anslyn EV, Krug RM, Ellington A, Robertus JD. Bioorg. Med. Chem. Lett. 2011; 21: 3007
- 14c Climent MJ, Corma A, Hernandez JC, Hungria AB, Iborra S, Martinez-Silvestre S. J. Catal. 2012; 292: 118
- 15a Martin LJ, Marzinzik AL, Ley SV, Baxendale IR. Org. Lett. 2011; 13: 320
- 15b Castillo J.-C, Presset M, Abonia R, Coquerel Y, Rodriguez J. Eur. J. Org. Chem. 2012; 2338
- 16 For alkenes, see: Attanasi OA, Crescentini LD, Filippone P, Mantellini F, Santeusanio S. Helv. Chim. Acta 2001; 84: 2379
- 17a Wang W, Shen Y, Meng X, Zhao M, Chen Y, Chen B. Org. Lett. 2011; 13: 4514
- 17b Xu Y, Wan X. Tetrahedron Lett. 2013; 54: 642
- 17c Shi S, Wang T, Yang W, Rudolph M, Hashmi AS. K. Chem. Eur. J. 2013; 19: 6576
- 18 Deng X, Mani NS. Org. Lett. 2006; 8: 269
- 19 Mousset C, Provot O, Hamze A, Bignon J, Brion J.-D, Alami M. Tetrahedron 2008; 64: 4287
- 20 Ren W, Xia Y, Ji S.-J, Zhang Y, Wan X, Zhao J. Org. Lett. 2009; 11: 1141
- 21 Zhang C, Jiao N. J. Am. Chem. Soc. 2010; 132: 28
- 22a Cai J.-J, Zou J.-P, Pan X.-Q, Zhang W. Tetrahedron Lett. 2008; 49: 7386
- 22b Liu Y, Chen X, Zhang J, Xu Z. Synlett 2013; 24: 1371
- 23 Rogatchov VO, Filimonov VD, Yusubov MS. Synthesis 2001; 1001
- 24 Chandrasekhar S, Reddy NK, Kumar VP. Tetrahedron Lett. 2010; 51: 3623
- 25 Chen C.-Y, Hu W.-P, Liu M.-C, Yan P.-C, Wang J.-J, Chung M.-I. Tetrahedron 2013; 69: 9735
- 26 Vadagaonkar KS, Kalmode HP, Murugan K, Chaskar AC. RSC Adv. 2015; 5: 5580
- 27 Viswanadham KK. D. R, Reddy MP, Sathyanarayana P, Ravi O, Kant R, Bathula SR. Chem. Commun. 2014; 50: 13517
- 28 Liu Y, Chen X, Zhang J, Xu Z. Synlett 2013; 24: 1371
- 29 CCDC 1437696 (5d), 1437784 (5f), 1048524 (5r), and 1048416 (6a) contain 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/getstructures.
- 30 Noolvi MN, Patel HM, Bhardwaj V, Chauhan A. Eur. J. Med. Chem. 2011; 46: 2327
- 31 Jeena V, Robinson RS. Tetrahedron Lett. 2014; 55: 642
- 32 Lian M, Li Q, Zhu Y, Yin G, Wu A. Tetrahedron 2012; 68: 9598
- 33 Katz M, Rakotomalala M, Voisin E, Williams VE, Bohne C, Pace TC. S. Can. J. Chem. 2011; 89: 297
- 34 Mamedov VA, Zhukova NA, Syakaev VV, Gubaidullin AT, Beschastnova TN, Adgamova DI, Samigullina AI, Latypov SK. Tetrahedron 2013; 69: 1403
- 35 Mahmoudi H, Malakooti R, Bardajee GR, Kakavand N. Catal. Lett. 2013; 143: 853
- 36 Drefahl G, Ploetner G. Chem. Ber. 1962; 95: 2782
- 37 Ghorbani-Vaghei R, Hajinazari S. J. Chem. Sci. 2013; 125: 353
- 38 Liu Y, Lou S, Xu Z, Zhang W. J. Org. Chem. 2013; 78: 5932
- 39 Al-Mourabit A, Nguyen TB, Retailleau P. Org Lett. 2013; 15: 5238
- 40 Aithagani SK, Singh PP, Singh VP, Vishwakarma RA, Yadav M. J. Org. Chem. 2013; 78: 2639
For ketones, see:
For 1,2-diketones, see:
For epoxides, see:
For vicinal diols, see:
For diazoketones, see:
For alkynes, see: