Download PDF
Müller, T. J. J.: 2014 Science of Synthesis, 2013/6: Multicomponent Reactions, Volume 2 DOI: 10.1055/sos-SD-211-00055
Multicomponent Reactions, Volume 2

2.1.4 Electron-Deficient Alkynes as Electrophiles

More Information

Book

Editor: Müller, T. J. J.

Authors: Alavijeh, N. S.; Arndtsen, B. A.; Balalaie, S.; Bonne, D.; Chen, C.; Coquerel, Y.; Elliott, M.; Festa, A.; Fusano, A.; Ghabraie, E.; Jones, D. H.; Modha, S.; Müller, T. J. J.; Purushothaman, S.; Raghunathan, R.; Rodriguez, J.-A.; Ryu, I.; Sarvary, A.; Shaabani, A.; Shaabani, S.; Szabó, K. J.; Takasu, K.; Tjutrins, J.; Van der Eycken, E.; Voskressensky, L.; Wan, J.; Xi, C.

Title: Multicomponent Reactions, Volume 2

Subtitle: Reactions Involving an α,α-Unsaturated Carbonyl Compound as Electrophilic Component, Cycloadditions, and Boron-, Silicon-, Free-Radical-, and Metal-Mediated Reactions

Print ISBN: 9783131728319; Online ISBN: 9783132064317; Book DOI: 10.1055/b-003-125831

1st edition © 2014. Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart

Subjects: Multicomponent Reactions

Science of Synthesis Reference Libraries



Parent publication

Title: Science of Synthesis

DOI: 10.1055/b-00000101

Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.

Type: Multivolume Edition

Also available at
 


Abstract

This chapter describes multicomponent reactions involving electron-deficient alkynes as electrophiles. The main focus is the addition of nucleophiles such as aza-aromatics, amines, and carbenes to electron-deficient alkynes in the presence of various suitable components such as CH-, NH-, and OH-acids, carbonyl and imine compounds, and electron-deficient alkenes. These multicomponent reactions result in the synthesis of various heterocyclic and open-chain organic products.

Key words

electron-deficient alkynes - carbonyl compounds - electrophile - nucleophile - heterocycles - cyclization
 
  • 1 Dömling A. Chem. Rev. 2006; 106: 17
    PubMed
  • 3 Ouellette RJ, Rawn JD. Organic Chemistry. Prentice-Hall; NJ 1996
    Google Scholar
  • 4 Shaabani A, Maleki A, Rezayan AH, Sarvary A. Mol. Diversity 2011; 15: 41
    PubMed
  • 5 Diels O, Alder K. Justus Liebigs Ann. Chem. 1932; 498: 16
  • 6 Acheson RM, Woollard J. J. Chem. Soc., Perkin Trans. 1 1975; 438
  • 7 Acheson RM, Taylor GA. Proc. Chem. Soc., London 1959; 186
  • 8 Acheson RM, Taylor GA. J. Chem. Soc. 1960; 1691
  • 9 Acheson RM, Plunket AO. J. Chem. Soc. 1964; 2676
  • 10 Huisgen R, Morikawa M, Herbig K, Brunn E. Chem. Ber. 1967; 100: 1094
  • 11 Nair V, Devipriya S, Eringathodi S. Tetrahedron Lett. 2007; 48: 3667
  • 12 Li M, Pan L, Wen L.-R. Helv. Chim. Acta 2011; 94: 169
  • 13 Adib M, Sheibani E, Mostofi M, Ghanbary K, Bijanzadeh HR. Tetrahedron 2006; 62: 3435
  • 14 Yavari I, Hosseini N, Moradi L. Monatsh. Chem. 2008; 139: 953
  • 15 Yavari I, Hossaini Z, Souri S, Seyfi S. Mol. Diversity 2009; 13: 439
    PubMed
  • 16 Nair V, Sreekanth AR, Biju AT, Rath NP. Tetrahedron Lett. 2003; 44: 729
  • 17 Nair V, Devipriya S, Suresh E. Tetrahedron 2008; 64: 3567
  • 18 Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-Darjani M. Monatsh. Chem. 2007; 138: 677
  • 19 Teimouri MB, Abbasi T, Ahmadian S, Poor Heravi MR, Bazhrang R. Tetrahedron 2009; 65: 8120
  • 20 Esmaeili AA, Vesalipoor H, Hosseinabadi R, Fakhari Zavareh A, Naseri MA, Ghiamati E. Tetrahedron Lett. 2011; 52: 4865
  • 21 Esmaeili AA, Nazer M. Synlett 2009; 2119
  • 22 Maghsoodlou MT, Habibi-Khorassani SM, Moradi A, Sajadikhah SS, Hazeri N, Davodi A. Tetrahedron 2011; 67: 8492
  • 23 Terzidis MA, Tsoleridis CA, Stephanidou-Stephanatou J. Synlett 2009; 229
  • 24 Subba Reddy BV, Yadav NN, Srivastava N, Yadav JS, Sridhar B. Helv. Chim. Acta 2012; 95: 76
  • 25 Xin Y, Zhao J, Zhu S. J. Fluorine Chem. 2012; 133: 97
  • 26 Nair V, Sreekanth AR, Abhilash N, Bhadbhade MM, Gonnade RC. Org. Lett. 2002; 4: 3575
    PubMed
  • 27 Shaabani A, Rezayan AH, Sarvary A, Khavasi HR. Tetrahedron Lett. 2008; 49: 1469
  • 28 Nair V, Devi BR, Varma LR. Tetrahedron Lett. 2005; 46: 5333
  • 29 Wang G.-W, Li J.-X. Org. Biomol. Chem. 2006; 4: 4063
    PubMed
  • 30 Yavari I, Ghazanfarpour-Darjani M, Sabbaghan M, Hossaini Z. Tetrahedron Lett. 2007; 48: 3749
  • 31 Nassiri M, Heydari R, Hazeri N, Habibi-Khorassani SM, Maghsoodlou MT, Jalili Milani F. ARKIVOC 2010; 61
  • 32 Ghahremanzadeh R, Ahadi S, Sayyafi M, Bazgir A. Tetrahedron Lett. 2008; 49: 4479
  • 33 Anary-Abbasinejad M, Mosslemin MH, Fazlinia A, Esfandiari H. Synth. Commun. 2010; 40: 385
  • 34 Nassiri M, Maghsoodlou MT, Heydari R, Habibi-Khorassani SM. Mol. Diversity 2008; 12: 111
    PubMed
  • 35 Xia E.-Y, Sun J, Yao R, Yan C.-G. Tetrahedron 2010; 66: 3569
  • 36 Yavari I, Anary-Abbasinejad M, Alizadeh A. Monatsh. Chem. 2002; 133: 1331
  • 37 Shaabani A, Soleimani E. Phosphorus, Sulfur Silicon Relat. Elem. 2006; 181: 2475
  • 38 Yavari I, Mokhtarporyani-Sanandaj A, Moradi L. Tetrahedron Lett. 2007; 48: 6709
  • 39 Shaabani A, Rezayan AH, Sarvary A, Heidary M, Ng SW. Tetrahedron 2009; 65: 6063
  • 40 Alizadeh A, Zohreh N. Helv. Chim. Acta 2008; 91: 844
  • 41 Adib M, Sheibani E, Zhu L.-G, Bijanzadeh HR. Tetrahedron Lett. 2009; 50: 4420
  • 42 Yadav JS, Subba Reddy BV, Yadav NN, Gupta MK. Tetrahedron Lett. 2008; 49: 2815
  • 43 Yavari I, Piltan M, Moradi L. Tetrahedron 2009; 65: 2067
  • 44 Yavari I, Hossaini Z, Sabbaghan M. Tetrahedron Lett. 2006; 47: 6037
  • 45 Yavari I, Sabbaghan M, Hossaini Z. Synlett 2006; 2501
  • 46 Bora U, Saikia A, Boruah RC. Org. Lett. 2003; 5: 435
    PubMed
  • 47 Yavari I, Mirzaei A, Moradi L, Hosseini N. Tetrahedron Lett. 2008; 49: 2355
  • 48 Yavari I, Mirzaei A, Moradi L, Khalili G. Tetrahedron Lett. 2010; 51: 396
  • 49 Yavari I, Karimi E. Tetrahedron Lett. 2008; 49: 6433
  • 50 Khaleghi F, Din LB, Jantan I, Yaacob WA, Khalilzadeh MA. Tetrahedron Lett. 2011; 52: 7182
  • 51 Yavari I, Mirzaei A, Moradi L. Synth. Commun. 2010; 40: 2407
  • 52 Shaabani A, Sarvary A, Mousavi-Faraz S, Ng SW. Monatsh. Chem. 2012; 143: 1061
  • 53 Yadav JS, Yadav NN, Subba Reddy BV, Gupta MK, Sridhar B. J. Org. Chem. 2008; 73: 6857
    PubMed
  • 54 Wu L, Sun J, Yan C. Chin. J. Chem. 2012; 30: 590
  • 55 Kumaraswamy G, Rambabu D, Jayaprakash N, Rao GV, Sridhar B. Eur. J. Org. Chem. 2009; 4158
  • 56 Yavari I, Nasiri-Gheidari S. Helv. Chim. Acta 2011; 94: 811
  • 57 Shen Y, Cai S, He C, Lin X, Lu P, Wang Y. Tetrahedron 2011; 67: 8338
  • 58 Adib M, Yavari H, Mollahosseini M. Tetrahedron Lett. 2004; 45: 1803
  • 59 Adib M, Mollahosseini M, Yavari H, Sayahi MH, Bijanzadeh HR. Synthesis 2004; 861
  • 60 Ma C, Ding H, Wang Y. Org. Lett. 2006; 8: 3133
    PubMed
  • 61 Elassar A.-ZS, El-Khair AA. Tetrahedron 2003; 59: 8463
  • 62 Liu W, Jiang H, Huang L. Org. Lett. 2010; 12: 312
    PubMed
  • 63 Yavari I, Bayat MJ. Tetrahedron Lett. 2011; 52: 6649
  • 64 Yavari I, Bayat MJ. Synlett 2010; 2293
  • 65 Anary-Abbasinejad M, Charkhati K, Anaraki-Ardakani H. Synlett 2009; 1115
  • 66 Ramesh K, Murthy SN, Karnakar K, Nageswar YVD. Tetrahedron Lett. 2011; 52: 3937
  • 67 Das B, Reddy GC, Balasubramanyam P, Veeranjaneyulu B. Synthesis 2010; 1625
  • 68 Nagarapu L, Mallepalli R, Yeramanchi L, Bantu R. Tetrahedron Lett. 2011; 52: 3401
  • 69 Ghabraie E, Balalaie S, Bararjanian M, Bijanzadeh HR, Rominger F. Tetrahedron 2011; 67: 5415
  • 70 Murthy SN, Madhav B, Kumar AV, Rao KR, Nageswar YVD. Tetrahedron 2009; 65: 5251
  • 71 Zhang M, Jiang H, Wang A. Synlett 2007; 3214
  • 72 Kiruthika SE, Amritha R, Perumal PT. Tetrahedron Lett. 2012; 53: 3268
  • 73 Teimouri MB, Abbasi T. Tetrahedron 2010; 66: 3795
  • 74 Yavari I, Seyfi S, Nematpour M, Hossaini Z. Helv. Chim. Acta 2010; 93: 1413
  • 75 Teimouri MB, Abbasi T, Mivehchi H. Tetrahedron 2008; 64: 10425
  • 76 Khan AT, Khan MM. Tetrahedron Lett. 2011; 52: 3455
  • 77 Alizadeh A, Sabahnoo H, Zohreh N, Noaparast Z, Zhu L.-G. Synlett 2011; 2495
  • 78 Yavari I, Souri S. Synlett 2007; 2969
  • 79 Yavari I, Souri S. Synlett 2008; 1208
  • 80 Ramesh K, Murthy SN, Nageswar YVD. Tetrahedron Lett. 2011; 52: 2362
  • 81 Yin G, Zhu Y, Lu P, Wang Y. J. Org. Chem. 2011; 76: 8922
    PubMed
  • 82 Xu J, Wei J, Bian L, Zhang J, Chen J, Deng H, Wu X, Zhang H, Cao W. Chem. Commun. (Cambridge) 2011; 47: 3607
    PubMed
  • 83 Alizadeh A, Rezvanian A. Synthesis 2008; 1747
  • 84 Alizadeh A, Movahedi F, Esmaili AA. Tetrahedron Lett. 2006; 47: 4469
  • 85 Alizadeh A, Rezvanian A, Zhu L.-G. Helv. Chim. Acta 2007; 90: 2414
  • 86 Alizadeh A, Babaki M, Zohreh N, Rezvanian A. Synthesis 2008; 3793
  • 87 Sun J, Wu Q, Xia E.-Y, Yan C.-G. Eur. J. Org. Chem. 2011; 2981
  • 88 Zhang M, Jiang H.-F. Eur. J. Org. Chem. 2008; 3519
  • 89 Zhu Q, Jiang H, Li J, Zhang M, Wang X, Qi C. Tetrahedron 2009; 65: 4604
  • 90 Cao H, Jiang H.-F, Qi C.-R, Yao W.-J, Chen H.-J. Tetrahedron Lett. 2009; 50: 1209
  • 91 Srikrishna A, Sridharan M, Prasad KR. Tetrahedron 2010; 66: 3651
  • 92 Zhang M, Jiang H, Liu H, Zhu Q. Org. Lett. 2007; 9: 4111
    PubMed
  • 93 Cao H, Wang X, Jiang H, Zhu Q, Zhang M, Liu H. Chem.–Eur. J. 2008; 14: 11623
    PubMed
  • 94 Zhu Q, Jiang H, Li J, Liu S, Xia C, Zhang M. J. Comb. Chem. 2009; 11: 685
    PubMed
  • 95 Khan AT, Ghosh A, Khan MM. Tetrahedron Lett. 2012; 53: 2622
  • 96 Sun J, Xia E.-Y, Wu Q, Yan C.-G. Org. Lett. 2010; 12: 3678
    PubMed
  • 97 Sun J, Sun Y, Xia E.-Y, Yan C.-G. ACS Comb. Sci. 2011; 13: 436
    PubMed
  • 98 Hadjebi M, Hashtroudi MS, Bijanzadeh HR, Balalaie S. Helv. Chim. Acta 2011; 94: 382
  • 99 Yamuna E, Zeller M, Prasad KJR. Tetrahedron Lett. 2011; 52: 6805
  • 100 Kiruthika SE, Lakshmi NV, Banu BR, Perumal PT. Tetrahedron Lett. 2011; 52: 6508
  • 101 Noroozi Tisseh Z, Ahmadi F, Dabiri M, Khavasi HR, Bazgir A. Tetrahedron Lett. 2012; 53: 3603
  • 102 Alizadeh A, Rezvanian A, Zhu L.-G. J. Org. Chem. 2012; 77: 4385
    PubMed
  • 103 Sun J, Sun Y, Gao H, Yan C.-G. Eur. J. Org. Chem. 2011; 6952
  • 104 Sun J, Xia E.-Y, Wu Q, Yan C.-G. ACS Comb. Sci. 2011; 13: 421
    PubMed
  • 105 Jiang H, Mai R, Ca H, Zhu Q, Liu X. Org. Biomol. Chem. 2009; 7: 4943
    PubMed
  • 106 Jiang H.-F, Li J.-H, Chen Z.-W. Tetrahedron 2010; 66: 9721
  • 107 Liu W.-B, Jiang H.-F, Zhu S.-F, Wang W. Tetrahedron 2009; 65: 7985
  • 108 Yavari I, Bayat MJ, Sirouspour M, Souri S. Tetrahedron 2010; 66: 7995
  • 109 Voskressensky LG, Kovaleva SA, Borisova TN, Listratova AV, Eresko AB, Tolkunov VS, Tolkunov SV, Varlamov AV. Tetrahedron 2010; 66: 9421
  • 110 Voskressensky L. G, Kulikova LN, Kasatochkina AS, Listratova AV, Toze FA, Borisova TN, Varlamov AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2010; 46: 1013
  • 111 Voskressensky LG, Kulikova LN, Kleimenov A, Guranova N, Borisova TN, Varlamov AV. Tetrahedron Lett. 2009; 50: 4851
  • 112 Lei M, Zhan Z, Tian W, Lu P. Tetrahedron 2012; 68: 3361
  • 113 Sabbaghan M, Yavari I, Hossaini Z, Souri S. Helv. Chim. Acta 2010; 93: 946
  • 114 Alizadeh A, Sheikhi E. Synthesis 2008; 1061
  • 115 Alizadeh A, Sheikhi E. Tetrahedron Lett. 2007; 48: 4887
  • 116 Bourissou D, Guerret O, Gabbai FP, Bertrand G. Chem. Rev. 2000; 100: 39
    PubMed
  • 117 Cheng Y, Meth-Cohn O. Chem. Rev. 2004; 104: 2507
    PubMed
  • 118 Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res. 2003; 36: 899
    PubMed
  • 119 Hoffmann RW, Lilienblum W, Dittrich B. Chem. Ber. 1974; 107: 3395
  • 120 Nair V, Bindu S, Balagopal L. Tetrahedron Lett. 2001; 42: 2043
  • 121 Nair V, Bindu S, Sreekumar V, Chiaroni A. Org. Lett. 2002; 4: 2821
    PubMed
  • 122 Nair V, Deepthi A, Poonoth M, Santhamma B, Vellalath S, Babu BP, Mohan R, Suresh E. J. Org. Chem. 2006; 71: 2313
    PubMed
  • 123 Nair V, Beneesh PB, Sreekumar V, Bindu S, Menon RS, Deepthi A. Tetrahedron Lett. 2005; 46: 201
  • 124 Enders D, Breuer K, Runsink J, Teles JH. Liebigs Ann. 1996; 2019
  • 125 Nair V, Mathew SC, Vellalath S, Pillai AN, Suresh E. Synthesis 2008; 551
  • 126 Nair V, Bindu S, Sreekumar V, Rath NP. Org. Lett. 2003; 5: 665
    PubMed
  • 127 Nair V, Sreekumar V, Bindu S, Suresh E. Org. Lett. 2005; 7: 2297
    PubMed
  • 128 Ma C, Ding H, Wu G, Yang Y. J. Org. Chem. 2005; 70: 8919
    PubMed
  • 129 Ma C, Yang Y. Org. Lett. 2005; 7: 1343
    PubMed
  • 130 Ding H, Zhang Y, Bian M, Yao W, Ma C. J. Org. Chem. 2008; 73: 578
    PubMed
  • 131 Ma C, Ding H, Zhang Y, Bian M. Angew. Chem. Int. Ed. 2006; 45: 7793
    PubMed
  • 132 Boominathan M, Nagaraj M, Muthusubramanian S, Krishnakumar RV. Tetrahedron 2011; 67: 6057
  • 133 Liu W.-B, Jiang H.-F, Qiao C.-L. Tetrahedron 2009; 65: 2110
  • 134 Sun J, Sun Y, Gao H, Yan C.-G. Eur. J. Org. Chem. 2012; 1976
  • 135 Yavari I, Kowsari E. Synlett 2008; 897
  • 136 Alizadeh A, Rezvanian A, Zhu L.-G. Tetrahedron 2008; 64: 351
  • 137 Xia S, Wang X, Ge Z, Cheng T, Li R. Tetrahedron 2009; 65: 1005
  • 138 Alizadeh A, Rostamnia S, Zohreh N, Hosseinpour R. Tetrahedron Lett. 2009; 50: 1533
  • 139 Souldozi A, Ramazani A, Dadrass AR, Ślepokura K, Lis T. Helv. Chim. Acta 2012; 95: 339
  • 140 Alizadeh A, Noaparast Z, Sabahno H, Zohreh N. Helv. Chim. Acta 2010; 93: 1401