2.1.4 Electron-Deficient Alkynes as Electrophiles

A. Shaabani; A. Sarvary; S. Shaabani

doi:10.1055/sos-SD-211-00055

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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

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Buch

Herausgeber: Müller, T. J. J.

Autoren: 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.

Titel: Multicomponent Reactions, Volume 2

Untertitel: 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; Buch-DOI: 10.1055/b-003-125831

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

Fachgebiete: Multikomponenten-Reaktionen

Science of Synthesis Reference Libraries

Übergeordnete Publikation

Titel: Science of Synthesis

DOI: 10.1055/b-00000101

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

Typ: Mehrbändiges Werk

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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.

Schlüsselwörter

electron-deficient alkynes - carbonyl compounds - electrophile - nucleophile - heterocycles - cyclization

1 Dömling A. Chem. Rev. 2006; 106: 17

PubMed Suche in Google Scholar

2 Zhu J, Bienaymé H. Multicomponent Reactions. Wiley-VCH; Weinheim, Germany 2005

Crossref Suche in Google Scholar

3 Ouellette RJ, Rawn JD. Organic Chemistry. Prentice-Hall; NJ 1996

Suche in Google Scholar

4 Shaabani A, Maleki A, Rezayan AH, Sarvary A. Mol. Diversity 2011; 15: 41

PubMed Suche in Google Scholar

5 Diels O, Alder K. Justus Liebigs Ann. Chem. 1932; 498: 16

Suche in Google Scholar

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

Suche in Google Scholar

11 Nair V, Devipriya S, Eringathodi S. Tetrahedron Lett. 2007; 48: 3667

Suche in Google Scholar

12 Li M, Pan L, Wen L.-R. Helv. Chim. Acta 2011; 94: 169

Suche in Google Scholar

13 Adib M, Sheibani E, Mostofi M, Ghanbary K, Bijanzadeh HR. Tetrahedron 2006; 62: 3435

Suche in Google Scholar

14 Yavari I, Hosseini N, Moradi L. Monatsh. Chem. 2008; 139: 953

Suche in Google Scholar

15 Yavari I, Hossaini Z, Souri S, Seyfi S. Mol. Diversity 2009; 13: 439

PubMed Suche in Google Scholar

16 Nair V, Sreekanth AR, Biju AT, Rath NP. Tetrahedron Lett. 2003; 44: 729

Suche in Google Scholar

17 Nair V, Devipriya S, Suresh E. Tetrahedron 2008; 64: 3567

Suche in Google Scholar

18 Yavari I, Hossaini Z, Sabbaghan M, Ghazanfarpour-Darjani M. Monatsh. Chem. 2007; 138: 677

Suche in Google Scholar

19 Teimouri MB, Abbasi T, Ahmadian S, Poor Heravi MR, Bazhrang R. Tetrahedron 2009; 65: 8120

Suche in Google Scholar

20 Esmaeili AA, Vesalipoor H, Hosseinabadi R, Fakhari Zavareh A, Naseri MA, Ghiamati E. Tetrahedron Lett. 2011; 52: 4865

Suche in Google Scholar

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

Suche in Google Scholar

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

Suche in Google Scholar

25 Xin Y, Zhao J, Zhu S. J. Fluorine Chem. 2012; 133: 97

Suche in Google Scholar

26 Nair V, Sreekanth AR, Abhilash N, Bhadbhade MM, Gonnade RC. Org. Lett. 2002; 4: 3575

PubMed Suche in Google Scholar

27 Shaabani A, Rezayan AH, Sarvary A, Khavasi HR. Tetrahedron Lett. 2008; 49: 1469

Suche in Google Scholar

28 Nair V, Devi BR, Varma LR. Tetrahedron Lett. 2005; 46: 5333

Suche in Google Scholar

29 Wang G.-W, Li J.-X. Org. Biomol. Chem. 2006; 4: 4063

PubMed Suche in Google Scholar

30 Yavari I, Ghazanfarpour-Darjani M, Sabbaghan M, Hossaini Z. Tetrahedron Lett. 2007; 48: 3749

Crossref Suche in Google Scholar

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

Suche in Google Scholar

33 Anary-Abbasinejad M, Mosslemin MH, Fazlinia A, Esfandiari H. Synth. Commun. 2010; 40: 385

Suche in Google Scholar

34 Nassiri M, Maghsoodlou MT, Heydari R, Habibi-Khorassani SM. Mol. Diversity 2008; 12: 111

PubMed Suche in Google Scholar

35 Xia E.-Y, Sun J, Yao R, Yan C.-G. Tetrahedron 2010; 66: 3569

Suche in Google Scholar

36 Yavari I, Anary-Abbasinejad M, Alizadeh A. Monatsh. Chem. 2002; 133: 1331

Suche in Google Scholar

37 Shaabani A, Soleimani E. Phosphorus, Sulfur Silicon Relat. Elem. 2006; 181: 2475

Suche in Google Scholar

38 Yavari I, Mokhtarporyani-Sanandaj A, Moradi L. Tetrahedron Lett. 2007; 48: 6709

Suche in Google Scholar

39 Shaabani A, Rezayan AH, Sarvary A, Heidary M, Ng SW. Tetrahedron 2009; 65: 6063

Suche in Google Scholar

40 Alizadeh A, Zohreh N. Helv. Chim. Acta 2008; 91: 844

Suche in Google Scholar

41 Adib M, Sheibani E, Zhu L.-G, Bijanzadeh HR. Tetrahedron Lett. 2009; 50: 4420

Suche in Google Scholar

42 Yadav JS, Subba Reddy BV, Yadav NN, Gupta MK. Tetrahedron Lett. 2008; 49: 2815

Suche in Google Scholar

43 Yavari I, Piltan M, Moradi L. Tetrahedron 2009; 65: 2067

Suche in Google Scholar

44 Yavari I, Hossaini Z, Sabbaghan M. Tetrahedron Lett. 2006; 47: 6037

Suche in Google Scholar

45 Yavari I, Sabbaghan M, Hossaini Z. Synlett 2006; 2501

46 Bora U, Saikia A, Boruah RC. Org. Lett. 2003; 5: 435

PubMed Suche in Google Scholar

47 Yavari I, Mirzaei A, Moradi L, Hosseini N. Tetrahedron Lett. 2008; 49: 2355

Suche in Google Scholar

48 Yavari I, Mirzaei A, Moradi L, Khalili G. Tetrahedron Lett. 2010; 51: 396

Suche in Google Scholar

49 Yavari I, Karimi E. Tetrahedron Lett. 2008; 49: 6433

Suche in Google Scholar

50 Khaleghi F, Din LB, Jantan I, Yaacob WA, Khalilzadeh MA. Tetrahedron Lett. 2011; 52: 7182

Suche in Google Scholar

51 Yavari I, Mirzaei A, Moradi L. Synth. Commun. 2010; 40: 2407

Suche in Google Scholar

52 Shaabani A, Sarvary A, Mousavi-Faraz S, Ng SW. Monatsh. Chem. 2012; 143: 1061

Suche in Google Scholar

53 Yadav JS, Yadav NN, Subba Reddy BV, Gupta MK, Sridhar B. J. Org. Chem. 2008; 73: 6857

PubMed Suche in Google Scholar

54 Wu L, Sun J, Yan C. Chin. J. Chem. 2012; 30: 590

Suche in Google Scholar

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

Crossref Suche in Google Scholar

57 Shen Y, Cai S, He C, Lin X, Lu P, Wang Y. Tetrahedron 2011; 67: 8338

Suche in Google Scholar

58 Adib M, Yavari H, Mollahosseini M. Tetrahedron Lett. 2004; 45: 1803

Suche in Google Scholar

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 Suche in Google Scholar

61 Elassar A.-ZS, El-Khair AA. Tetrahedron 2003; 59: 8463

Suche in Google Scholar

62 Liu W, Jiang H, Huang L. Org. Lett. 2010; 12: 312

PubMed Suche in Google Scholar

63 Yavari I, Bayat MJ. Tetrahedron Lett. 2011; 52: 6649

Suche in Google Scholar

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

Suche in Google Scholar

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

Suche in Google Scholar

69 Ghabraie E, Balalaie S, Bararjanian M, Bijanzadeh HR, Rominger F. Tetrahedron 2011; 67: 5415

Suche in Google Scholar

70 Murthy SN, Madhav B, Kumar AV, Rao KR, Nageswar YVD. Tetrahedron 2009; 65: 5251

Suche in Google Scholar

71 Zhang M, Jiang H, Wang A. Synlett 2007; 3214

72 Kiruthika SE, Amritha R, Perumal PT. Tetrahedron Lett. 2012; 53: 3268

Suche in Google Scholar

73 Teimouri MB, Abbasi T. Tetrahedron 2010; 66: 3795

Suche in Google Scholar

74 Yavari I, Seyfi S, Nematpour M, Hossaini Z. Helv. Chim. Acta 2010; 93: 1413

Suche in Google Scholar

75 Teimouri MB, Abbasi T, Mivehchi H. Tetrahedron 2008; 64: 10425

Suche in Google Scholar

76 Khan AT, Khan MM. Tetrahedron Lett. 2011; 52: 3455

Suche in Google Scholar

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

Suche in Google Scholar

81 Yin G, Zhu Y, Lu P, Wang Y. J. Org. Chem. 2011; 76: 8922

PubMed Suche in Google Scholar

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 Suche in Google Scholar

83 Alizadeh A, Rezvanian A. Synthesis 2008; 1747

84 Alizadeh A, Movahedi F, Esmaili AA. Tetrahedron Lett. 2006; 47: 4469

Suche in Google Scholar

85 Alizadeh A, Rezvanian A, Zhu L.-G. Helv. Chim. Acta 2007; 90: 2414

Suche in Google Scholar

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

Suche in Google Scholar

90 Cao H, Jiang H.-F, Qi C.-R, Yao W.-J, Chen H.-J. Tetrahedron Lett. 2009; 50: 1209

Suche in Google Scholar

91 Srikrishna A, Sridharan M, Prasad KR. Tetrahedron 2010; 66: 3651

Suche in Google Scholar

92 Zhang M, Jiang H, Liu H, Zhu Q. Org. Lett. 2007; 9: 4111

PubMed Suche in Google Scholar

93 Cao H, Wang X, Jiang H, Zhu Q, Zhang M, Liu H. Chem.–Eur. J. 2008; 14: 11623

PubMed Suche in Google Scholar

94 Zhu Q, Jiang H, Li J, Liu S, Xia C, Zhang M. J. Comb. Chem. 2009; 11: 685

PubMed Suche in Google Scholar

95 Khan AT, Ghosh A, Khan MM. Tetrahedron Lett. 2012; 53: 2622

Suche in Google Scholar

96 Sun J, Xia E.-Y, Wu Q, Yan C.-G. Org. Lett. 2010; 12: 3678

PubMed Suche in Google Scholar

97 Sun J, Sun Y, Xia E.-Y, Yan C.-G. ACS Comb. Sci. 2011; 13: 436

PubMed Suche in Google Scholar

98 Hadjebi M, Hashtroudi MS, Bijanzadeh HR, Balalaie S. Helv. Chim. Acta 2011; 94: 382

Suche in Google Scholar

99 Yamuna E, Zeller M, Prasad KJR. Tetrahedron Lett. 2011; 52: 6805

Suche in Google Scholar

100 Kiruthika SE, Lakshmi NV, Banu BR, Perumal PT. Tetrahedron Lett. 2011; 52: 6508

Suche in Google Scholar

101 Noroozi Tisseh Z, Ahmadi F, Dabiri M, Khavasi HR, Bazgir A. Tetrahedron Lett. 2012; 53: 3603

Suche in Google Scholar

102 Alizadeh A, Rezvanian A, Zhu L.-G. J. Org. Chem. 2012; 77: 4385

PubMed Suche in Google Scholar

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 Suche in Google Scholar

105 Jiang H, Mai R, Ca H, Zhu Q, Liu X. Org. Biomol. Chem. 2009; 7: 4943

PubMed Suche in Google Scholar

106 Jiang H.-F, Li J.-H, Chen Z.-W. Tetrahedron 2010; 66: 9721

Suche in Google Scholar

107 Liu W.-B, Jiang H.-F, Zhu S.-F, Wang W. Tetrahedron 2009; 65: 7985

Suche in Google Scholar

108 Yavari I, Bayat MJ, Sirouspour M, Souri S. Tetrahedron 2010; 66: 7995

Suche in Google Scholar

109 Voskressensky LG, Kovaleva SA, Borisova TN, Listratova AV, Eresko AB, Tolkunov VS, Tolkunov SV, Varlamov AV. Tetrahedron 2010; 66: 9421

Suche in Google Scholar

110 Voskressensky L. G, Kulikova LN, Kasatochkina AS, Listratova AV, Toze FA, Borisova TN, Varlamov AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2010; 46: 1013

Suche in Google Scholar

111 Voskressensky LG, Kulikova LN, Kleimenov A, Guranova N, Borisova TN, Varlamov AV. Tetrahedron Lett. 2009; 50: 4851

Suche in Google Scholar

112 Lei M, Zhan Z, Tian W, Lu P. Tetrahedron 2012; 68: 3361

Suche in Google Scholar

113 Sabbaghan M, Yavari I, Hossaini Z, Souri S. Helv. Chim. Acta 2010; 93: 946

Suche in Google Scholar

114 Alizadeh A, Sheikhi E. Synthesis 2008; 1061

115 Alizadeh A, Sheikhi E. Tetrahedron Lett. 2007; 48: 4887

Suche in Google Scholar

116 Bourissou D, Guerret O, Gabbai FP, Bertrand G. Chem. Rev. 2000; 100: 39

PubMed Suche in Google Scholar

117 Cheng Y, Meth-Cohn O. Chem. Rev. 2004; 104: 2507

PubMed Suche in Google Scholar

118 Nair V, Rajesh C, Vinod AU, Bindu S, Sreekanth AR, Mathen JS, Balagopal L. Acc. Chem. Res. 2003; 36: 899

PubMed Suche in Google Scholar

119 Hoffmann RW, Lilienblum W, Dittrich B. Chem. Ber. 1974; 107: 3395

Suche in Google Scholar

120 Nair V, Bindu S, Balagopal L. Tetrahedron Lett. 2001; 42: 2043

Suche in Google Scholar

121 Nair V, Bindu S, Sreekumar V, Chiaroni A. Org. Lett. 2002; 4: 2821

PubMed Suche in Google Scholar

122 Nair V, Deepthi A, Poonoth M, Santhamma B, Vellalath S, Babu BP, Mohan R, Suresh E. J. Org. Chem. 2006; 71: 2313

PubMed Suche in Google Scholar

123 Nair V, Beneesh PB, Sreekumar V, Bindu S, Menon RS, Deepthi A. Tetrahedron Lett. 2005; 46: 201

Suche in Google Scholar

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 Suche in Google Scholar

127 Nair V, Sreekumar V, Bindu S, Suresh E. Org. Lett. 2005; 7: 2297

PubMed Suche in Google Scholar

128 Ma C, Ding H, Wu G, Yang Y. J. Org. Chem. 2005; 70: 8919

PubMed Suche in Google Scholar

129 Ma C, Yang Y. Org. Lett. 2005; 7: 1343

PubMed Suche in Google Scholar

130 Ding H, Zhang Y, Bian M, Yao W, Ma C. J. Org. Chem. 2008; 73: 578

PubMed Suche in Google Scholar

131 Ma C, Ding H, Zhang Y, Bian M. Angew. Chem. Int. Ed. 2006; 45: 7793

PubMed Suche in Google Scholar

132 Boominathan M, Nagaraj M, Muthusubramanian S, Krishnakumar RV. Tetrahedron 2011; 67: 6057

Suche in Google Scholar

133 Liu W.-B, Jiang H.-F, Qiao C.-L. Tetrahedron 2009; 65: 2110

Suche in Google Scholar

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

Suche in Google Scholar

137 Xia S, Wang X, Ge Z, Cheng T, Li R. Tetrahedron 2009; 65: 1005

Suche in Google Scholar

138 Alizadeh A, Rostamnia S, Zohreh N, Hosseinpour R. Tetrahedron Lett. 2009; 50: 1533

Suche in Google Scholar

139 Souldozi A, Ramazani A, Dadrass AR, Ślepokura K, Lis T. Helv. Chim. Acta 2012; 95: 339

Suche in Google Scholar

140 Alizadeh A, Noaparast Z, Sabahno H, Zohreh N. Helv. Chim. Acta 2010; 93: 1401

Suche in Google Scholar