Related E-Products
Related Journals
Related Books
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.xmlSynthesis 2012; 44(9): 1279-1292
DOI: 10.1055/s-0031-1289749
DOI: 10.1055/s-0031-1289749
review
The Cyanamide Moiety, Synthesis and Reactivity
Marie-Hélène Larraufie
a UPMC Université Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France
,
Giovanni Maestri
a UPMC Université Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France
,
Max Malacria
a UPMC Université Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France
,
Cyril Ollivier
a UPMC Université Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France
,
Louis Fensterbank*
a UPMC Université Paris 06, Institut Parisien de Chimie Moléculaire (UMR CNRS 7201), 4 place Jussieu, C. 229, 75005 Paris, France
,
Emmanuel Lacôte*
b ICSN CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette Cedex, France, Fax: +33(1)44277360; +33(1)69077247 Email:louis.fensterbank@upmc.fr Email:emmanuel.lacote@icsn.cnrs-gif.fr
› Author AffiliationsFurther Information
Publication History
Received: 17 January 2012
Accepted after revision: 20 February 2012
Publication Date:
12 April 2012 (online)
Abstract
The cyanamide moiety provides many opportunities as a building block for the synthesis of nitrogen-containing heterocycles. This review discusses the reported methods for the preparation of alkyl- andN-acylcyanamides and illustrates their reactivity vis-à-vis nucleophilic additions, cycloadditions, radical chemistry and coordination chemistry.
1Introduction
2Biological Relevance of the Cyanamide Moiety
3Access to Cyanamides
3.1Cyanation of Amines
3.2Palladium Catalysis
3.3Deoxygenation of Isocyanates
3.4Desulfurization of Thioureas
4Reactivity of Cyanamides
4.1Nucleophilic Additions
4.2Cycloadditions
4.3Additions to Carbonyl Groups
4.4Chlorinations and Oxidations withtert-Butyl-N-chlorocyanamide
4.5Cyanamides as Radical Partners
5Coordination Chemistry of Cyanamides
6Conclusion
References
- 1 Nekrasov DD.Russ. J. Org. Chem. 2004; 40: 1387
- 2 Kamo T, Endo M, Sato M, Kasahara R, Yamaya H, Hiradate S, Fujii Y, Hirai N, Hirota M.Phytochemistry 2008; 69: 1166
- 3 Loomis CW, Brien JF.Can. J. Phys. Pharmacol. 1983; 61: 1025
- 4 Niederhofer H, Staffen W, Mair A.Alcohol and Alcoholism 2003; 38: 50
- 5a Duvernay F, Chiavassa T, Borget F, Aycard JP.J. Am. Chem. Soc. 2004; 126: 7772
- 5b Duvernay F, Chiavassa T, Borget F, Aycard JP.J. Phys. Chem. 2005; 109: 603
- 6 Anastasi C, Crowe MA, Powner MW, Sutherland JD.Angew. Chem. Int. Ed. 2006; 45: 6176
- 7 Ronn R, Gossas T, Sabnis YA, Daoud H, Akerblom E, Danielson UH, Sandstrom A.Bioorg. Med. Chem. 2007; 15: 4057
- 8a Falgueyret JP, Oballa RM, Okamoto O, Wesolowski G, Aubin Y, Rydzewski RM, Prasit P, Riendeau D, Rodan SB, Percival MD.J. Med. Chem. 2001; 44: 94
- 8b Barrett DG, Deaton DN, Hassell AM, McFadyen RB, Miller AB, Miller LR, Payne JA, Shewchuk LM, Willard DH, Wright LL.Bioorg. Med. Chem. Lett. 2005; 15: 3039
- 9 Demko ZP, Sharpless KB.Org. Lett. 2001; 3: 4091
- 10 Rogister F, Laeckmann D, Plasman PO, Van Eylen F, Ghyoot M, Maggetto C, Liegeois JF, Geczy J, Herchuelz A, Delarge J, Masereel B.Eur. J. Med. Chem. 2001; 36: 597
- 11 Domling A, Herdtweck E, Heck S.Tetrahedron Lett. 2006; 47: 1745
- 12 Xiao ZL, Yang MG, Tebben AJ, Galella MA, Weinstein DS.Tetrahedron Lett. 2010; 51: 5843
- 13 Cockerill AF, Deacon A, Harrison RG, Osborne DJ, Prime DM, Ross WJ, Todd A, Verge JP.Synthesis 1976; 591
- 14 Lindsey CC, O’Boyle BM, Mercede SJ, Pettus TR. R.Tetrahedron Lett. 2004; 45: 867
- 15 Kumar V, Kaushik MP, Mazumdar A.Eur. J. Org. Chem. 2008; 1910
- 16 Servais A, Azzouz M, Lopes D, Courillon C, Malacria M.Angew. Chem. Int. Ed. 2007; 46: 576
- 17 von Braun J.Ber. Dtsch. Chem. Ges. 1900; 33: 1438
- 18 Giles RL, Sullivan JD, Steiner AM, Looper RE.Angew. Chem. Int. Ed. 2009; 48: 3116
- 19 McCall WS, Grillo TA, Comins DL.J. Org. Chem. 2008; 73: 9744
- 20 McCall WS, Comins DL.Org. Lett. 2009; 11: 2940
- 21 Kim JJ, Kweon DH, Cho SD, Kim HK, Jung EY, Lee SG, Falck JR, Yoon YJ.Tetrahedron 2005; 61: 5889
- 22 Wu YQ, Limburg DC, Wilkinson DE, Hamilton GS.Org. Lett. 2000; 2: 795
- 23a Kamijo S, Jin T, Yamamoto Y.Angew. Chem. Int. Ed. 2002; 41: 1780
- 23b Kamijo S, Jin TN, Yamamoto Y.J. Am. Chem. Soc. 2001; 123: 9453
- 23c Kamijo S, Yamamoto Y.J. Am. Chem. Soc. 2002; 124: 11940
- 24 Stolley RM, Guo W, Louie J.Org. Lett. 2012; 14: 322
- 25 Wong FF, Chen CY, Yeh MY.Synlett 2006; 559
- 26 Chen CY, Wong FF, Huang JJ, Lin SK, Yeh M.Tetrahedron Lett. 2008; 49: 6505
- 27 Brand H, Mayer P, Schulz A, Soller T, Villinger A.Chem.–Asian J. 2008; 3: 1050
- 28 Ghosh H, Yella R, Ali AR, Sahoo SK, Patel BK.Tetrahedron Lett. 2009; 50: 2407
- 29a Nath J, Patel BK, Jamir L, Sinha UB, Satyanarayana K.Green Chem. 2009; 11: 1503
- 29b Yella R, Khatun N, Rout SK, Patel BK.Org. Biomol. Chem. 2011; 9: 3235
- 30 Yella R, Kavala V, Patel BK.Synth. Commun. 2011; 41: 792
- 31 Ramana T, Punniyamurthy T.Eur. J. Org. Chem. 2011; 4756
- 32 Ramana T, Saha P, Das M, Punniyamurthy T.Org. Lett. 2010; 12: 84
- 33a Davies M, Jones WJ.Trans. Faraday Soc. 1958; 54: 1454
- 33b Fukurnoto K, Oya T, Itazaki M, Nakazawa H.J. Am. Chem. Soc. 2009; 131: 38
- 34 Koroleva EV, Ignatovich ZhV, Ignatovich SV, Gusak KN.Russ. J. Org. Chem. 2011; 47: 1222
- 35 Oballa RM, Truchon JF, Bayly CI, Chauret N, Day S, Crane S, Berthelette C.Bioorg. Med. Chem. Lett. 2007; 17: 998
- 36a Chen CY, Lin HC, Huang YY, Chen KL, Huang JJ, Yeh MY, Wong FF.Tetrahedron 2010; 66: 1892
- 36b Shestakov AS, Gusakova NV, Shikhaliev KS, Zagoruiko AV.Russ. J. Gen. Chem. 2006; 76: 1647
- 36c Snider BB, Ahn Y, O’Hare SM.Org. Lett. 2001; 3: 4217
- 36d Prashad M, Har D, Chen LJ, Kim HY, Repic O, Blacklock TJ.J. Org. Chem. 2002; 67: 6612
- 37 Kohn U, Klopfleisch M, Gorls H, Anders E.Tetrahedron: Asymmetry 2006; 17: 811
- 38 Snider BB, O‘Hare SM.Tetrahedron Lett. 2001; 42: 2455
- 39 Zhou L, Chen J, Zhou J, Yeung Y.-Y.Org. Lett. 2011; 13: 5804
- 40 Shikhaliev KS, Shestakov AS, Medvedeva SM, Gusakova NV.Russ. Chem. Bull. 2008; 57: 170
- 41 Shestakov AS, Gusakova NV, Shikhaliev KS, Timoshkina AG.Russ. J. Org. Chem. 2007; 43: 1825
- 42 Giles RL, Nkansah RA, Looper RE.J. Org. Chem. 2010; 75: 261
- 43 Dutta S, Higginson CJ, Ho BT, Rynearson KD, Dibrov SM, Hermann T.Org. Lett. 2010; 12: 360
- 44 Castilla J, Marin I, Matheu MI, Diaz Y, Castillon S.J. Org. Chem. 2010; 75: 514
- 45 Kumar V, Rana H, Sankolli R, Kaushik MP.Tetrahedron Lett. 2011; 52: 6148
- 46 Snider BB, Duvall JR.Org. Lett. 2005; 7: 4519
- 47a Pratap R, Farahanullah; Raghunandan R, Maulik PR, Ram VJ.Tetrahedron Lett. 2007; 48: 4939
- 47b Farhanullah; Agarwal N, Goel A, Ram V.J. Org. Chem. 2003; 68: 2983
- 48 Pawlas J, Begtrup M.Org. Lett. 2002; 4: 2687
- 49 Kurzer F.J. Chem. Soc. 1949; 3033
- 50 Chen X, Bai SD, Wang L, Liu DS.Heterocycles 2005; 65: 1425
- 51 Herrera A, Martinez-Alvarez R, Ramiro P, Chioua M, Chioua R.Synthesis 2004; 503
- 52 Foster BJ, Harding BJ, Leylandjones B, Hoth D.Cancer Treat. Rev. 1986; 13: 197
- 53 Dornan P, Rowley CN, Priem J, Barry ST, Burchell TJ, Woo TK, Richeson DS.Chem. Commun. 2008; 3645
- 54 Heller B, Sundermann B, Buschmann H, Drexler HJ, You JS, Holzgrabe U, Heller E, Oehme G.J. Org. Chem. 2002; 67: 4414
- 55a Boñaga LV. R, Zhang HC, Moretto AF, Ye H, Gauthier DA, Li J, Leo GC, Maryanoff BE.J. Am. Chem. Soc. 2005; 127: 3473
- 55b Bonaga LV. R, Zhang HC, Maryanoff BE.Chem. Commun. 2004; 2394
- 55c Maryanoff BE, Zhang HC.ARKIVOC 2007; (xii): 7
- 56a Varela JA, Saa C.Chem. Rev. 2003; 103: 3787
- 56b Dazinger G, Torres-Rodrigues M, Kirchner K, Calhorda MJ, Costa PJ.J. Organomet. Chem. 2006; 691: 4434
- 57 Garcia P, Evanno Y, George P, Sevrin M, Ricci G, Malacria M, Aubert C, Gandon V.Org. Lett. 2011; 13: 2030
- 58 Geny A, Agenet N, Iannazzo L, Malacria M, Aubert C, Gandon V.Angew. Chem. Int. Ed. 2009; 48: 1810
- 59 Hapko M, Kral K, Fischer C, Spannenberg A, Gutnov A, Redkin D, Heller B.J. Org. Chem. 2010; 75: 3993
- 60 Tanaka K, Suzuki N, Nishida G.Eur. J. Org. Chem. 2006; 3917
- 61 Stolley RM, Maczka MT, Louie J.Eur. J. Org. Chem. 2011; 3815
- 62a Demko ZP, Sharpless KB.J. Org. Chem. 2001; 66: 7945
- 62b Habibi D, Nasrollahzadeh M, Faraji AR, Bayat Y.Tetrahedron 2010; 66: 3866
- 63 Nasrollahzadeh M, Habibi D, Shahkarami Z, Bayat Y.Tetrahedron 2009; 65: 10715
- 64 Masuda JD, Martin D, Lyon-Saunier C, Baceiredo A, Gornitzka H, Donnadieu B, Bertrand G.Chem.–Asian J. 2007; 2: 178
- 65a Bhattacharyya P, Slawin AM. Z, Woollins JD.Chem.–Eur. J. 2002; 8: 2705
- 65b Hua GX, Zhang QZ, Li Y, Slawin AM. Z, Woollins JD.Tetrahedron 2009; 65: 6074
- 66 Hulme R, Zamora OD. P, Mota EJ, Pasten MA, Contreras-Rojas R, Miranda R, Valencia-Hernandez I, Correa-Basurto J, Trujillo-Ferrara J, Delgado F.Tetrahedron 2008; 64: 3372
- 67 Khatab TK, El-Bayouki KA. M, Basyouni WM.Tetrahedron Lett. 2011; 52: 1448
- 68 Aberle NS, Lessene G, Watson KG.Org. Lett. 2006; 8: 419
- 69 Yin P, Ma WB, Chen Y, Huang WC, Deng Y, He L.Org. Lett. 2009; 11: 5482
- 70 Herrera A, Martinez-Alvarez R, Chioua R, Benabdelouahab F, Chioua M.Tetrahedron 2004; 60: 5475
- 71 Jenkinson SF, Jones NA, Moussa A, Stewart AJ, Heinz T, Fleet GW. J.Tetrahedron Lett. 2007; 48: 4441
- 72 Kumar V, Kaushik MP.Synlett 2007; 2937
- 73 Kumar V, Kaushik MP.Tetrahedron Lett. 2006; 47: 1457
- 74 Kumar V, Kaushik MP.Bull. Chem. Soc. Jpn. 2008; 81: 160
- 75 Beaume A, Courillon C, Derat E, Malacria M.Chem.–Eur. J. 2008; 14: 1238
- 76 Zard SZ.Chem. Soc. Rev. 2008; 37: 1603
- 77 Larraufie M.-H, Courillon C, Ollivier C, Lacôte E, Malacria M, Fensterbank L.J. Am. Chem. Soc. 2010; 132: 4381
- 78 Larraufie M.-H, Ollivier C, Fensterbank L, Malacria M, Lacôte E.Angew. Chem. Int. Ed. 2010; 49: 2178
- 79 Hu Z, Li SD, Hong PZ.ARKIVOC 2010; (ix): 171
- 80 Martin A, Perez-Martin I, Suarez E.Tetrahedron 2009; 65: 6147
- 81 Lindsey CC, O’Boyle BM, Mercede SJ, Pettus TR. R, Crutchley RJ.Coord. Chem. Rev. 2001; 219: 125
- 82 Khorasani-Motlagh M, Safari N, Noroozifar M, Shahroosvand H, Patrick BO.Inorg. Chim. Acta 2009; 362: 1260
- 83 Rezvani AR, Hadadzadeh H, Patrick B.Inorg. Chim. Acta 2002; 336: 125
- 84 Khorasani-Motlagh M, Noroozifar M, Niromand S, Khajeh S, Patrick BO.Inorg. Chim. Acta 2009; 362: 3785
- 85 Hadadzadeh H, Rezvani R, Esfandiari H.Polyhedron 2008; 27: 1809
- 86 Mohammad Nezhad J, Safari N.Inorg. Chim. Acta 2009; 362: 2782
- 87a Al-Noaimi M, Yap GP. A, Crutchley RJ.Inorg. Chem. 2004; 43: 1770
- 87b Mapolelo DT, Al-Noalmi M, Crutchley RJ.Inorg. Chim. Acta 2006; 359: 1458
- 88a Al-Noaimi M, Crutchley RJ.Inorg. Chim. Acta 2007; 360: 3013
- 88b Chisholm MH, D’Acchioli JS, Hadad CM, Patmore NJ.Inorg. Chem. 2006; 45: 11035
- 89 Dudd L, Hart M, Ring D, Sondaz E, Bonvoisin J, Coppel Y.Inorg. Chem. Commun. 2003; 6: 1400
- 90 Baker A, Jaud J, Launay JP, Bonvoisin J.Inorg. Chim. Acta 2005; 358: 3513
- 91 Fabre MA, Jaud J, Bonvoisin J.Inorg. Chim. Acta 2005; 358: 2384
- 92 Escuer A, McKee V, Nelson J, Ruiz E, Sanz N, Vicente R.Chem.–Eur. J. 2005; 11: 398
- 93a Yuan M, Zhao F, Zhang W, Pan F, Wang ZM, Gao S.Chem.–Eur. J. 2007; 13: 2937
- 93b Wang XY, Wang ZM, Gao S.Chem. Commun. 2008; 281
- 94 Kang LC, Chen X, Wang XS, Li YZ, Song Y, Zuo JL, You XZ.Dalton Trans. 2011; 40: 5200
- 95a Batten SR, Murray KS.Coord. Chem. Rev. 2003; 246: 103
- 95b Turner DR, Chesman AS, Murray KS, Deacon GB, Batten SR.Chem. Commun. 2011; 10189
- 96 Tanabe Y, Kajitani H, Iwasaki M, Ishii Y.Dalton Trans. 2007; 36: 4701
- 97 Imaji M, Tanabe Y, Mutoh Y, Ishii Y.Inorg. Chem. 2009; 48: 773
- 98 Gushchin PV, Kuznetsov ML, Haukka M, Wang MJ, Gribanov AV, Kukushkin VY.Inorg. Chem. 2009; 48: 2583
- 99 Vicente J, Abad JA, Lopez-Saez MJ, Jones PG, Bautista D.Chem.–Eur. J. 2010; 16: 661
- 100 Bardaji M, Laguna A, Perez MR, Jones PG.Organometallics 2002; 21: 1877