18.13.2 Guanidine Derivatives (Update 2019)

Abstract

This chapter is an update to the earlier Science of Synthesis contribution (Section 18.13) on the preparation of guanidines, as well on their applications in organic synthesis. It focuses on the literature published in the period 2004–2017.

Key words

guanidines - cyanamides - carbodiimides - isocyanates - isothiocyanates - ureas - thioureas - isothioureas - isocyanides

• 1 Alonso-Moreno C, Antiñolo A, Carrillo-Hermosilla F, Otero A. Chem. Soc. Rev. 2014; 43: 3406

• 2 Lemrová B, Soural M. Eur. J. Org. Chem. 2015; 1869

• 3 Looper RE, Haussener TJ, Mack JBC. J. Org. Chem. 2011; 76: 6967

• 4 Köhn U, Klopfleisch M, Görls H, Anders E. Tetrahedron: Asymmetry 2006; 17: 811

• 5 Maestri G, Larraufie M.-H, Ollivier C, Malacria M, Fensterbank L, Lacôte E. Org. Lett. 2012; 14: 5538

• 6 Lachs JR, Barrett AGM, Crimmin MR, Kociok-Köhn G, Hill MS, Mahon MF, Procopiou PA. Eur. J. Inorg. Chem. 2008; 4173

• 7 Shen H, Chan H.-S, Xie Z. Organometallics 2006; 25: 5515

• 8 Zhang W.-X, Nishiura M, Hou Z. Chem.–Eur. J. 2007; 13: 4037

• 9 Chen J, Wang Y, Luo Y. Chin. J. Chem. 2013; 31: 1065

• 10 Zhang W.-X, Nishiura M, Hou Z. Synlett 2006; 1213

• 11 Du Z, Li W, Zhu X, Xu F, Shen Q. J. Org. Chem. 2008; 73: 8966

• 12 Li Q, Wang S, Zhou S, Yang G, Zhu X, Liu Y. J. Org. Chem. 2007; 72: 6763

• 13 Li Z, Xue M, Yao H, Sun H, Zhang Y, Shen Q. J. Organomet. Chem. 2012; 713: 27

• 14 Montilla F, del Río D, Pastor A, Galindo A. Organometallics 2006; 25: 4996

• 15 Zhang X, Wang C, Qian C, Han F, Xu F, Shen Q. Tetrahedron 2011; 67: 8790

• 16 Tu J, Li W, Xue M, Zhang Y, Shen Q. Dalton Trans. 2013; 42: 5890

• 17 Zhang W.-X, Li D, Wang Z, Xi Z. Organometallics 2009; 28: 882

• 18 Zhu X, Xu F, Shen Q. Chin. Sci. Bull. 2012; 57: 3419

• 19 Li D, Guang J, Zhang W.-X, Wang Y, Xi Z. Org. Biomol. Chem. 2010; 8: 1816

• 20 Zhu X, Du Z, Xu F, Shen Q. J. Org. Chem. 2009; 74: 6347

• 21 Pottabathula S, Royo B. Tetrahedron Lett. 2012; 53: 5156

• 22 Baishya A, Peddarao T, Barman MK, Nembenna S. New J. Chem. 2015; 39: 7503

• 23 Shainyan BA, Tolstikova LL, Schilde U. J. Fluorine Chem. 2012; 135: 261

• 24 Chen C.-Y, Lin H.-C, Huang Y.-Y, Chen K.-L, Huang J.-J, Yeh M.-Y, Wong FF. Tetrahedron 2010; 66: 1892

• 25 Åkerbladh L, Schembri LS, Larhed M, Odell LR. J. Org. Chem. 2017; 82: 12 520

• 26 Li J, Neuville L. Org. Lett. 2013; 15: 6124

• 27 Li J, Wang H, Hou Y, Yu W, Xu S, Zhang Y. Eur. J. Org. Chem. 2016; 2388

• 28 Zhou L, Chen J, Zhou J, Yeung Y.-Y. Org. Lett. 2011; 13: 5804

• 29 Huang N.-Y, Liu M.-G, Ding M.-W. J. Org. Chem. 2009; 74: 6874

• 30 Soleiman HA. Int. J. Chem. (Toronto, ON, Can.) 2014; 6: 55

• 31 Hirota S, Kato R, Suzuki M, Soneta Y, Otani T, Saito T. Eur. J. Org. Chem. 2008; 2075

• 32 Vvedensky VY, Rogovoy BV, Kiselyov AS, Ivachtchenko AV. Tetrahedron Lett. 2005; 46: 8699

• 33 Kumar R, Ermolat’ev DS, Van der Eycken EV. J. Org. Chem. 2013; 78: 5737

• 34 Pape S, Wessig P, Brunner H. RSC Adv. 2015; 5: 101 408

• 35 Pape S, Wessig P, Brunner H. J. Org. Chem. 2016; 81: 4701

• 36 Cunha S, Rodrigues MT. Tetrahedron Lett. 2006; 47: 6955

• 37 Qin C, Li J, Fan E. Synlett 2009; 2465

• 38 Li J, Mi Y, He J, Luo X, Fan E. J. Heterocycl. Chem. 2013; 50: 304

• 39 Ohara K, Vasseur J.-J, Smietana M. Tetrahedron Lett. 2009; 50: 1463

• 40 Dangate PS, Akamanchi KG. Tetrahedron Lett. 2012; 53: 6765

• 41 Ramadas K, Janarthanan N, Pritha R. Synlett 1997; 1053

• 42 Porcheddu A, De Luca L, Giacomelli G. Synlett 2009; 3368

• 43 Pattarawarapan M, Jaita S, Wangngae S, Phakhodee W. Tetrahedron Lett. 2016; 57: 1354

• 44 Maki T, Tsuritani T, Yasukata T. Org. Lett. 2014; 16: 1868

• 45 Shinada T, Umezawa T, Ando T, Kozuma H, Ohfune Y. Tetrahedron Lett. 2006; 47: 1945

• 46 Isobe T, Fukuda K, Tokunaga T, Seki H, Yamaguchi K, Ishikawa T. J. Org. Chem. 2000; 65: 7774

• 47 Maryanoff CA, Stanzione RC, Plampin JN, Mills JE. J. Org. Chem. 1986; 51: 1882

• 48 Mohanazadeh F, Nami N, Hosseini SS. Chin. J. Chem. 2011; 29: 1055

• 49 Esteves H, de Fátima Â, Castro RdeP, Sabino JR, Macedo F, Brito TO. Tetrahedron Lett. 2015; 56: 6872

• 50 Molina P, Alajarín M, Saez J. Synth. Commun. 1983; 13: 67

• 51 Horner L, Oediger H. Justus Liebigs Ann. Chem. 1959; 627: 142

• 52 Ube H, Uraguchi D, Terada M. J. Organomet. Chem. 2007; 692: 545

• 53 Yuan JH, Yang XX, Lin H, Wang DX. Chin. Chem. Lett. 2011; 22: 1399

• 54 Aoyagi N, Endo T. Synth. Commun. 2017; 47: 442

• 55 Sandin H, Swanstein M.-L, Wellner E. J. Org. Chem. 2004; 69: 1571

• 56 Burgess K, Lim D, Ho K.-K, Ke C.-Y. J. Org. Chem. 1994; 59: 2179

• 57 Ma D, Xia C, Jiang J, Zhang J. Org. Lett. 2001; 3: 2189

• 58 Santana AG, Francisco CG, Suárez E, González CC. J. Org. Chem. 2010; 75: 5371

• 59 More SS, Raghunadh A, Shankar R, Patel NB, Bhalerao DS, Kumar UKS. Helv. Chim. Acta 2014; 97: 404

• 60 Tamaki M, Han G, Hruby VJ. J. Org. Chem. 2001; 66: 1038

• 61 Xia C, Heng L, Ma D. Tetrahedron Lett. 2002; 43: 9405

• 62 Le Corre L, Kizirian J.-C, Levraud C, Boucher J.-L, Bonnet V, Dhimane H. Org. Biomol. Chem. 2008; 6: 3388

• 63 Hernández D, Lindsay KB, Nielsen L, Mittag T, Bjerglund K, Friis S, Mose R, Skrydstrup T. J. Org. Chem. 2010; 75: 3283

• 64 Craig W, Chen J, Richardson D, Thorpe R, Yuan Y. Org. Lett. 2015; 17: 4620

• 65 Thai K, Clement CW, Gravel M. Tetrahedron Lett. 2009; 50: 6540

• 66 Castillo-Meléndez JA, Golding BT. Synthesis 2004; 1655

• 67 Porcheddu A, Giacomelli G, Chighine A, Masala S. Org. Lett. 2004; 6: 4925

• 68 Cortes-Salva M, Nguyen B.-L, Cuevas J, Pennypacker KR, Antilla JC. Org. Lett. 2010; 12: 1316

• 69 Xing H, Zhang Y, Lai Y, Jiang Y, Ma D. J. Org. Chem. 2012; 77: 5449

• 70 Hammoud H, Schmitt M, Bihel F, Antheaume C, Bourguignon J.-J. J. Org. Chem. 2012; 77: 417

• 71 Miyabe H, Yoshida K, Reddy VK, Takemoto Y. J. Org. Chem. 2009; 74: 305 J. Org. Chem. 2009; 74: 1428

• 72 Larraufie M.-H, Ollivier C, Fensterbank L, Malacria M, Lacôte E. Angew. Chem. 2010; 122: 2224 Angew. Chem. Int. Ed. 2010; 49: 2178

• 73 Yang D, Wang Y, Yang H, Liu T, Fu H. Adv. Synth. Catal. 2012; 354: 477

• 74 Schmuck C, Wienand W. J. Am. Chem. Soc. 2003; 125: 452

• 75 Schmuck C, Bickert V, Merschky M, Geiger L, Rupprecht D, Dudaczek J, Wich P, Rehm T, Machon U. Eur. J. Org. Chem. 2008; 324

• 76 Rether C, Schmuck C. Eur. J. Org. Chem. 2011; 1459

• 77 Hulme R, Zamora ODP, Mota EJ, Pastén MA, Contreras-Rojas R, Miranda R, Valencia-Hernández I, Correa-Basurto J, Trujillo-Ferrara J, Delgado F. Tetrahedron 2008; 64: 3372

• 78 Moustafa AH, Shestakov AS, Shikhaliev KS. Chem. Heterocycl. Compd. (Engl. Transl.) 2012; 48: 613 Khim. Geterotsikl. Soedin. 2012; 658

• 79 Carbajales C, Azuaje J, Oliveira A, Loza MI, Brea J, Cadavid MI, Masaguer CF, García-Mera X, Gutiérrez-de-Terán H, Sotelo E. J. Med. Chem. 2017; 60: 3372

• 80 Kunkel H, Maas G. Eur. J. Org. Chem. 2007; 3746

• 81 Shah J, Liebscher J. Synthesis 2008; 917

• 82 Hövelmann CH, Streuff J, Brelot L, Muñiz K. Chem. Commun. (Cambridge) 2008; 2334

• 83 Muñiz K, Hövelmann CH, Streuff J, Campos-Gómez E. Pure Appl. Chem. 2008; 80: 1089

• 84 Muñiz K, Streuff J, Hövelmann CH, Núñez A. Angew. Chem. 2007; 119: 7255 Angew. Chem. Int. Ed. 2007; 46: 7125

• 85 Mailyan AK, Young K, Chen JL, Reid BT, Zakarian A. Org. Lett. 2016; 18: 5532

• 86 Garlets ZJ, Silvi M, Wolfe JP. Org. Lett. 2016; 18: 2331

• 87 Daniel M, Blanchard F, Nocquet-Thibault S, Cariou K, Dodd RH. J. Org. Chem. 2015; 80: 10 624

• 88 Al Shuhaib Z, Davies DH, Dennis M, Evans DM, Fletcher MD, Franken H, Hancock P, Hollinshead J, Jones I, Kähm K, Murphy PJ, Nash R, Potter D, Rowles R. Tetrahedron 2014; 70: 4412

• 89 Zavesky BP, Babij NR, Fritz JA, Wolfe JP. Org. Lett. 2013; 15: 5420

• 90 Gainer MJ, Bennett NR, Takahashi Y, Looper RE. Angew. Chem. 2011; 123: 710 Angew. Chem. Int. Ed. 2011; 50: 684

• 91 Tian G, Fedoseev P, Van der Eycken EV. Chem.–Eur. J. 2017; 23: 5224

• 92 Singh RP, Das J, Yousufuddin M, Gout D, Lovely CJ. Org. Lett. 2017; 19: 4110

• 93 Al-Shuhaib Z, Böckemeier H, Coghlan L, Dörksen E, Jones IV, Murphy PJ, Nash R, Page JM. Tetrahedron Lett. 2013; 54: 6716

• 94 L’abbé G, Verbruggen A, Minami T, Toppet S. J. Org. Chem. 1981; 46: 4478

• 95 Zhao B, Du H, Shi Y. Org. Lett. 2008; 10: 1087

• 96 Zhao B, Peng X, Zhu Y, Ramirez TA, Cornwall RG, Shi Y. J. Am. Chem. Soc. 2011; 133: 20 890

• 97 Mestres R, Palomo C. Synthesis 1980; 755

• 98 Quast H, Schmitt E. Angew. Chem. 1969; 81: 428 Angew. Chem. Int. Ed. Engl. 1969; 8: 448

• 99 Zhu T.-H, Wang S.-Y, Wei T.-Q, Ji S.-J. Adv. Synth. Catal. 2015; 357: 823

• 100 Zhang Z, Li Z, Fu B, Zhang Z. Chem. Commun. (Cambridge) 2015; 51: 16 312

• 101 Qiao G, Zhang Z, Huang B, Zhu L, Xiao F, Zhang Z. Synthesis 2018; 50: 330

• 102 Baeten M, Maes BUW. Adv. Synth. Catal. 2016; 358: 826

• 103 Wangngae S, Pattarawarapan M, Phakhodee W. Synlett 2016; 27: 1121

• 104 Wangngae S, Pattarawarapan M, Phakhodee W. J. Org. Chem. 2017; 82: 10 331

• 105 Castagnolo D, Raffi F, Giorgi G, Botta M. Eur. J. Org. Chem. 2009; 334

• 106 Feichtinger K, Zapf C, Sings HL, Goodman M. J. Org. Chem. 1998; 63: 3804

• 107 Usachev S, Gridnev A. Synth. Commun. 2011; 41: 3683

• 108 Hickey SM, Ashton TD, Khosa SK, Pfeffer FM. Synlett 2012; 23: 1779