PDF icon PDF herunterladen
Synthesis 2010(4): 694-700  
DOI: 10.1055/s-0029-1218583
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

‘Ligand-Free-Like’ CuCl-Catalyzed Atom Transfer Radical Cyclization of N-Substituted N-Allyl Polychloroamides to γ-Lactams

Mariella Pattarozzi*, Fabrizio Roncaglia, Valerio Giangiordano, Paolo Davoli, Fabio Prati, Franco Ghelfi*
Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, 41100 Modena, Italy
Fax: +39(059)373543; e-Mail: franco.ghelfi @unimore.it;
Weitere Informationen

Publikationsverlauf

Received 19 October 2009
Publikationsdatum:
27. November 2009 (online)

   Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

Erratum zu diesem Artikel:

‘Ligand-Free-Like’ CuCl-Catalyzed Atom Transfer Radical Cyclization of N-Substituted N-Allyl Polychloroamides to γ-LactamsSynthesis 2010; 2010(04): e2-e2
DOI: 10.1055/s-0029-1218659

Abstract

Atom transfer radical cyclization (ATRC) of N-alkyl N-allyl dichloroamides to γ-lactams, catalyzed by ‘naked’ CuCl, worked efficiently in DMF, whereas, when the same dichloro­amides were N-sulfonylated, DMF needed to be replaced by acetonitrile. The outcome of the cycloisomerization with N-substituted N-allyl trichloroacetamides was less affected by solvent choice, although for an effective reaction to occur, the solvent had to dissolve the cuprous salt. Catalyst loading ranged between 5 and 20 mol%.

Key words

amides - copper - cyclizations - lactams - radical reactions

    References

  • 1a Majumdar KC. Basu PK. González A. Curr. Org. Chem.  2009,  13:  599 
    Suche in Google Scholar
  • 1b Yoshioka E. Kohtani S. Miyabe H. Heterocycles  2009,  79:  229 
    Suche in Google Scholar
  • 1c Majumdar KC. Basu PK. Chattopadhyay SK. Tetrahedron  2007,  63:  793 
    Suche in Google Scholar
  • 1d Srikanth GSC. Castle SL. Tetrahedron  2005,  61:  10377 
    Suche in Google Scholar
  • 1e Bowman WR. Fletcher AJ. Potts GBS. J. Chem. Soc., Perkin Trans. 1  2002,  2747 
  • 1f Galeazzi R. Mobbili G. Orena M. In Targets in Heterocyclic Systems. Chemistry and Properties   Vol. 1:  Attanasi OA. Spinelli D. RCS Publishing; Cambridge: 1997.  p.355 
    Suche in Google Scholar
  • 1g Giese B. Kopping B. Göbel T. Dickhaut J. Thoma G. Kulicke KJ. Trach F. Org. React.  1996,  48:  301 
    Suche in Google Scholar
  • 1h Ishibashi H. Sato T. Ikeda M. J. Synth. Org. Chem.  1995,  53:  85 
    Suche in Google Scholar
  • 2a Pudlo M. Gérard S. Mirand C. Sapi J. Tetrahedron Lett.  2008,  49:  1066 
    Suche in Google Scholar
  • 2b Miyabe H. Asada R. Toyoda A. Takemoto Y. Angew. Chem. Int. Ed.  2006,  45:  5863 
    Suche in Google Scholar
  • 2c Ueda M. Miyabe H. Nishimura A. Miyata O. Takemoto Y. Naito T. Org. Lett.  2003,  5:  3835 
    Suche in Google Scholar
  • 2d Wang C. Russell GA. J. Org. Chem.  1999,  64:  2346 
    Suche in Google Scholar
  • 2e De Riggi I. Gastaldi S. Surzur J.-M. Bertrand MP. J. Org. Chem.  1992,  57:  6118 
    Suche in Google Scholar
  • 2f Chuang C.-P. Tetrahedron  1991,  47:  5425 
    Suche in Google Scholar
  • 3 Bertrand MP. Nouguier R. Archavlis A. Carrière A. Synlett  1994,  736 
    Thieme Connect
  • 4a Asahi K. Nishino H. Synthesis  2009,  409 
  • 4b Taylor EC. Liu B. J. Org. Chem.  2001,  66:  3726 
    Suche in Google Scholar
  • 4c Cossy J. Bouzide A. Leblanc C. J. Org. Chem.  2000,  65:  7257 
    Suche in Google Scholar
  • 4d Galeazzi R. Mobbili G. Orena M. Tetrahedron  1996,  52:  1069 
    Suche in Google Scholar
  • 5 Nair V. Mohanan K. Suja TD. Biju AT. Synthesis  2007,  1179 
    Thieme Connect
  • 6a Xu X. Che X. Gao S. Wu J. Bai X. Synlett  2005,  1865 
  • 6b Rancourt J. Gorys V. Jolicoeur E. Tetrahedron Lett.  1998,  39:  5339 
    Suche in Google Scholar
  • 6c Curran DP. Yu H. Lu H. Tetrahedron  1994,  50:  7343 
    Suche in Google Scholar
  • 7a Taniguchi T. Kawajiri R. Ishibashi H. ARKIVOC  2008,  (xiv):  7 
    Suche in Google Scholar
  • 7b Rodríguez-Soria V. Quintero L. Sartillo-Piscil F. Tetrahedron Lett.  2007,  48:  4305 
    Suche in Google Scholar
  • 7c Bowman WR. Krintel SL. Schilling MB. Synlett  2004,  1215 
  • 7d Aszodi J. Rowlands DA. Mauvais P. Collette P. Bonnefoy A. Lampilas M. Bioorg. Med. Chem. Lett.  2004,  14:  2489 
    Suche in Google Scholar
  • 7e Bryans JS. Large JM. Parsons AF. J. Chem. Soc., Perkin Trans. 1  1999,  2897 
  • 7f Bryans JS. Large JM. Parsons AF. J. Chem. Soc., Perkin Trans. 1  1999,  2905 
  • 7g Sato T. Tsujimoto K. Matsubayashi K. Ishibashi H. Ikeda M. Chem. Pharm. Bull.  1992,  40:  2308 ; and references cited therein
    Suche in Google Scholar
  • 7h Stork G. Mah R. Heterocycles  1989,  28:  723 
    Suche in Google Scholar
  • 8a Rodríguez-Soria V. Quintero L. Sartillo-Piscil F. Tetrahedron  2008,  64:  2750 
    Suche in Google Scholar
  • 8b Cao L. Li C. Tetrahedron Lett.  2008,  49:  7380 
    Suche in Google Scholar
  • 8c Hernán AG. Kilburn JD. Tetrahedron Lett.  2004,  45:  831 
    Suche in Google Scholar
  • 8d Yang D. Yan Y.-L. Law K.-L. Zhu N.-Y. Tetrahedron  2003,  59:  10465 
    Suche in Google Scholar
  • 8e Yorimitsu H. Oshima K. Bull. Chem. Soc. Jpn.  2002,  75:  853 
    Suche in Google Scholar
  • 8f Gilbert BC. Kalz W. Lindsay CI. McGrail PT. Parsons AF. Whittaker DTE. J. Chem. Soc., Perkin Trans. 1  2000,  1187 
  • 8g Ikeda M. Teranishi H. Nozaki K. Ishibashi H. J. Chem. Soc., Perkin Trans. 1  1998,  1691 
  • 8h Ozaki S. Matsushita H. Emoto M. Ohmori H. Chem. Pharm. Bull.  1995,  43:  32 
    Suche in Google Scholar
  • 8i Curran DP. Tamine J. J. Org. Chem.  1991,  56:  2746 
    Suche in Google Scholar
  • 9a El Kaïm L. Grimaud L. Miranda LD. Vieu E. Tetrahedron Lett.  2006,  47:  8259 
    Suche in Google Scholar
  • 9b Bertin D. Gigmes D. Marque SRA. Tordo P. Tetrahedron  2005,  61:  8752 
    Suche in Google Scholar
  • 9c Axon J. Boiteau L. Boivin J. Forbes JE. Zard SZ. Tetrahedron Lett.  1994,  35:  1719 
    Suche in Google Scholar
  • 9d Byers JH. Gleason TG. Knight KS. J. Chem. Soc., Chem. Commun.  1991,  355 
  • For reactions that can be formally considered to belong to the group, see:
  • 9e Cassayre J. Dauge D. Zard SZ. Synlett  2000,  471 
  • 9f Uneyama K. J. Organomet. Chem.  2000,  611:  158 
    Suche in Google Scholar
  • 10a Rowlands GJ. Tetrahedron  2009,  65:  8603 
    Suche in Google Scholar
  • 10b Alcaide B. Almendros P. Luna A. Chem. Rev.  2009,  109:  3817 
    Suche in Google Scholar
  • 10c Clark AJ. Chem. Soc. Rev.  2002,  31:  1 
    Suche in Google Scholar
  • 10d Nagashima H. Itoh K. J. Synth. Org. Chem., Jpn.  1995,  53:  298 
    Suche in Google Scholar
  • 10e Iqbak J. Bathia B. Nayyar NK. Chem. Rev.  1994,  94:  519 
    Suche in Google Scholar
  • 11a Matyjaszewski K. Xia J. Chem. Rev.  2001,  101:  2921 
    Suche in Google Scholar
  • 11b Kamigaito M. Ando T. Sawamoto M. Chem. Rev.  2001,  101:  3689 
    Suche in Google Scholar
  • 11c Poli R. Angew. Chem. Int. Ed.  2006,  45:  5058 
    Suche in Google Scholar
  • 12a Ghelfi F. Pattarozzi M. Roncaglia F. Parsons AF. Felluga F. Pagnoni UM. Valentin E. Mucci A. Bellesia F. Synthesis  2008,  3131 
  • 12b Bull JA. Hutchings MG. Luján C. Quayle P. Tetrahedron Lett.  2008,  49:  1356 
    Suche in Google Scholar
  • 12c Clark AJ. Geden JV. Thom S. J. Org. Chem.  2006,  71:  1471 
    Suche in Google Scholar
  • 12d Bellesia F. Danieli C. De Buyck L. Galeazzi R. Ghelfi F. Mucci A. Orena M. Pagnoni UM. Parsons AF. Roncaglia F. Tetrahedron  2006,  62:  746 
    Suche in Google Scholar
  • 12e De Buyck L. Danieli C. Ghelfi F. Pagnoni UM. Parsons AF. Pattarozzi M. Roncaglia F. Tetrahedron  2005,  60:  2871 
    Suche in Google Scholar
  • 12f Masahiko I. Masahiko S. Hitoshi N. Hiroshi K. Hiroshi Y. Pest Manag. Sci.  2004,  60:  981 
    Suche in Google Scholar
  • 12g Cagnoli R. Ghelfi F. Pagnoni UM. Parsons AF. Schenetti L. Tetrahedron  2003,  59:  9951 
    Suche in Google Scholar
  • 12h Bryans JS. Chessum NEA. Huther N. Parsons AF. Ghelfi F. Tetrahedron  2003,  59:  6221 
    Suche in Google Scholar
  • 12i Kawano T. Kuwana J. Shinomaru T. Du C.-X. Ueda I. Chem. Lett.  2001,  1230 
  • 12j Clark AJ. Battle GM. Hemings AM. Haddlenton DM. Bridge A. Tetrahedron Lett.  2001,  42:  2003 
    Suche in Google Scholar
  • 12k Nagashima H. Isono Y. Iwamatsu S. J. Org. Chem.  2001,  66:  315 
    Suche in Google Scholar
  • 12l Ghelfi F. Parsons AF. J. Org. Chem.  2000,  65:  6249 
    Suche in Google Scholar
  • 12m Clark AJ. Filik RP. Haddleton DM. Radigue A. Sanders CJ. Thomas GH. Smith ME. J. Org. Chem.  1999,  64:  8954 
    Suche in Google Scholar
  • 12n Clark AJ. Filik RP. Thomas GH. Tetrahedron Lett.  1999,  40:  4885 
    Suche in Google Scholar
  • 12o Iwamatsu S. Kondo H. Matsubara K. Nagashima H. Tetrahedron  1999,  55:  1687 
    Suche in Google Scholar
  • 12p Clark AJ. Duncalf DJ. Filik RP. Haddleton DM. Thomas GH. Wongtap H. Tetrahedron Lett.  1999,  40:  3807 
    Suche in Google Scholar
  • 12q Ghelfi F. Bellesia F. Forti L. Ghirardini G. Grandi R. Libertini E. Montemaggi M. Pagnoni UM. Pinetti A. De Buyck L. Parsons AF. Tetrahedron  1999,  55:  5839 
    Suche in Google Scholar
  • 12r Iwamatsu S. Matsubara K. Nagashima H. J. Org. Chem.  1999,  64:  9625 
    Suche in Google Scholar
  • 12s Baldovini N. Bertrand M.-P. Carrière A. Nouguier R. Plancher J.-M. J. Org. Chem.  1996,  61:  3205 
    Suche in Google Scholar
  • 12t Benedetti M. Forti L. Ghelfi F. Pagnoni UM. Ronzoni R. Tetrahedron  1997,  53:  14031 
    Suche in Google Scholar
  • 12u Nagashima H. Ozaki N. Ishii M. Seki K. Washiyama M. Itoh K. J. Org. Chem.  1993,  58:  464 
    Suche in Google Scholar
  • 13a Moryyasu K, Tomitani K, Miura T, Nishida M, Hibi S, Oda K, and Hayashi M. inventors; JP  04193877. 
  • 13b Broadhurst MD, and Gless RD. inventors; US  4645843. 
  • 13c Wollard FX. inventors; EP 0134564  A. 
  • 13d Broadhurst MD. inventors; EP 0129296  A1. 
  • 13e Rempfler H, and Meyer W. inventors; EP 0055215  A1. 
  • 14a Dutta B. Scoppelliti R. Severin K. Organometallics  2008,  27:  423 
    Suche in Google Scholar
  • 14b Edlin CD. Faulkner J. Fengas D. Helliwell M. Knight CK. House D. Parker J. Preece I. Quayle P. Raftery J. Richards SN. J. Organomet. Chem.  2006,  691:  5375 
    Suche in Google Scholar
  • 14c Motoyama Y. Hanada S. Shimamoto N. Nagashima H. Tetrahedron  2006,  62:  2779 
    Suche in Google Scholar
  • 14d Motoyama Y. Hanada S. Niibayashi S. Shimamoto K. Takaoka N. Nagashima H. Tetrahedron  2005,  61:  10216 
    Suche in Google Scholar
  • 14e Seigal BA. Fajardo C. Snapper ML. J. Am. Chem. Soc.  2005,  127:  16329 
    Suche in Google Scholar
  • 14f Rachita MA. Slough GA. Tetrahedron Lett.  1993,  34:  6821 
    Suche in Google Scholar
  • 14g Ishibashi H. Uemura N. Nakatani H. Okazaki M. Sato T. Nakamura N. Ikeda M. J. Org. Chem.  1993,  58:  2360 
    Suche in Google Scholar
  • 14h Nagashima H. Wakamatsu H. Ozaki N. Ishii T. Watanabe M. Tajima T. Itoh K. J. Org. Chem.  1992,  57:  1682 
    Suche in Google Scholar
  • 15a Braunecker WA. Matyjaszewski K. Prog. Polym. Sci.  2007,  32:  93 
    Suche in Google Scholar
  • 15b Pintauer T. Matyjaszewski K. Chem. Soc. Rev.  2008,  37:  1087 
    Suche in Google Scholar
  • 16a Clark AJ. Tetrahedron Lett.  2008,  49:  4848 
    Suche in Google Scholar
  • 16b Wolf J. Thommes K. Briel O. Scoppelliti R. Severin K. Organometallics  2008,  27:  4464 
    Suche in Google Scholar
  • 16c Thommes K. Içli B. Scoppelliti R. Severin K. Chem. Eur. J.  2007,  13:  6899 
    Suche in Google Scholar
  • 17 Zhu R. Xing L. Wang X. Cheng C. Su D. Hu Y. Adv. Synth. Catal.  2008,  350:  1253 
    CrossrefSuche in Google Scholar
  • 18a Bellu D. Pure Appl. Chem.  1985,  57:  1827 
    Suche in Google Scholar
  • 18b Kobrakov KI. Ivanov AV. Chem. Heterocycl. Compd. (Engl. Trans.)  2001,  37:  529 
    Suche in Google Scholar
  • 19a Seijas JA. Vázquez-Tato MP. Castedo L. Estévez RJ. Ónega MG. Ruiz M. Tetrahedron  1992,  48:  1637 
    Suche in Google Scholar
  • 19b Nagashima H. Ozaky N. Seki K. Ishii M. Itoh K. J. Org. Chem.  1989,  54:  4496 
    Suche in Google Scholar
  • 19c Nagashima H. Ara K. Wakamatsu H. Itoh K. J. Chem. Soc., Chem. Commun.  1985,  518 
  • 19d Nagashima H. Wakamatsu H. Itoh K. J. Chem. Soc., Chem. Commun.  1984,  652 
  • 19e Broadhurst MD. inventors; US  4132713. 
  • 19f Tseng CK. Teach EG. Simons RW. Synth. Commun.  1984,  14:  1027 
    Suche in Google Scholar
  • 19g Teach EG. inventors; US  4210589. 
  • 19h Teach EG. inventors; US  4119636. 
  • 19i Teach EG. inventors; DE  2612731. 
  • 20a Nenaidenko VG. Korotchenko VN. Shastin AV. Tyurin DA. Balenkova ES. Russ. J. Org. Chem.  2004,  40:  1750 
    Suche in Google Scholar
  • 20b Channon M. Rajzmann M. Channon F. Tetrahedron  1990,  46:  6193 
    Suche in Google Scholar
  • 20c Timokhin BV. Russ. Chem. Rev.  1990,  59:  193 
    Suche in Google Scholar
  • 21a Muzart J. Tetrahedron  2009,  65:  8313 
    Suche in Google Scholar
  • 21b Karpinets AP. Ukr. Khim. Zh. (Russ. Ed.)  2000,  66:  29 ; Chem. Abstr. 2000, 134, 5189
    Suche in Google Scholar
  • 21c Khobayashi S. Yasuda M. Hachiya I. Chem. Lett.  1996,  407 
  • 21d Freidlina RK. Chukovskaya EC. Synthesis  1974,  477