‘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

doi:10.1055/s-0029-1218583

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.xml

Share / Bookmark

Facebook X Linkedin Weibo

Download PDF

Synthesis 2010(4): 694-700
DOI: 10.1055/s-0029-1218583

PAPER

‘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;

Further Information

Publication History

Received 19 October 2009
Publication Date:
27 November 2009 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

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

Google Scholar
1b Yoshioka E. Kohtani S. Miyabe H. Heterocycles 2009, 79: 229

Google Scholar
1c Majumdar KC. Basu PK. Chattopadhyay SK. Tetrahedron 2007, 63: 793

Google Scholar
1d Srikanth GSC. Castle SL. Tetrahedron 2005, 61: 10377

Google Scholar
1e Bowman WR. Fletcher AJ. Potts GBS. J. Chem. Soc., Perkin Trans. 1 2002, 2747

Google Scholar
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

Google Scholar
1g Giese B. Kopping B. Göbel T. Dickhaut J. Thoma G. Kulicke KJ. Trach F. Org. React. 1996, 48: 301

Google Scholar
1h Ishibashi H. Sato T. Ikeda M. J. Synth. Org. Chem. 1995, 53: 85

Google Scholar
2a Pudlo M. Gérard S. Mirand C. Sapi J. Tetrahedron Lett. 2008, 49: 1066

Google Scholar
2b Miyabe H. Asada R. Toyoda A. Takemoto Y. Angew. Chem. Int. Ed. 2006, 45: 5863

Google Scholar
2c Ueda M. Miyabe H. Nishimura A. Miyata O. Takemoto Y. Naito T. Org. Lett. 2003, 5: 3835

Google Scholar
2d Wang C. Russell GA. J. Org. Chem. 1999, 64: 2346

Google Scholar
2e De Riggi I. Gastaldi S. Surzur J.-M. Bertrand MP. J. Org. Chem. 1992, 57: 6118

Google Scholar
2f Chuang C.-P. Tetrahedron 1991, 47: 5425

Google Scholar
3 Bertrand MP. Nouguier R. Archavlis A. Carrière A. Synlett 1994, 736

Article in Thieme Connect Google Scholar
4a Asahi K. Nishino H. Synthesis 2009, 409

Google Scholar
4b Taylor EC. Liu B. J. Org. Chem. 2001, 66: 3726

Google Scholar
4c Cossy J. Bouzide A. Leblanc C. J. Org. Chem. 2000, 65: 7257

Google Scholar
4d Galeazzi R. Mobbili G. Orena M. Tetrahedron 1996, 52: 1069

Google Scholar
5 Nair V. Mohanan K. Suja TD. Biju AT. Synthesis 2007, 1179

Article in Thieme Connect Google Scholar
6a Xu X. Che X. Gao S. Wu J. Bai X. Synlett 2005, 1865

Google Scholar
6b Rancourt J. Gorys V. Jolicoeur E. Tetrahedron Lett. 1998, 39: 5339

Google Scholar
6c Curran DP. Yu H. Lu H. Tetrahedron 1994, 50: 7343

Google Scholar
7a Taniguchi T. Kawajiri R. Ishibashi H. ARKIVOC 2008, (xiv): 7

Google Scholar
7b Rodríguez-Soria V. Quintero L. Sartillo-Piscil F. Tetrahedron Lett. 2007, 48: 4305

Google Scholar
7c Bowman WR. Krintel SL. Schilling MB. Synlett 2004, 1215

Google Scholar
7d Aszodi J. Rowlands DA. Mauvais P. Collette P. Bonnefoy A. Lampilas M. Bioorg. Med. Chem. Lett. 2004, 14: 2489

Google Scholar
7e Bryans JS. Large JM. Parsons AF. J. Chem. Soc., Perkin Trans. 1 1999, 2897

Google Scholar
7f Bryans JS. Large JM. Parsons AF. J. Chem. Soc., Perkin Trans. 1 1999, 2905

Google Scholar
7g Sato T. Tsujimoto K. Matsubayashi K. Ishibashi H. Ikeda M. Chem. Pharm. Bull. 1992, 40: 2308 ; and references cited therein

Google Scholar
7h Stork G. Mah R. Heterocycles 1989, 28: 723

Google Scholar
8a Rodríguez-Soria V. Quintero L. Sartillo-Piscil F. Tetrahedron 2008, 64: 2750

Google Scholar
8b Cao L. Li C. Tetrahedron Lett. 2008, 49: 7380

Google Scholar
8c Hernán AG. Kilburn JD. Tetrahedron Lett. 2004, 45: 831

Google Scholar
8d Yang D. Yan Y.-L. Law K.-L. Zhu N.-Y. Tetrahedron 2003, 59: 10465

Google Scholar
8e Yorimitsu H. Oshima K. Bull. Chem. Soc. Jpn. 2002, 75: 853

Google Scholar
8f Gilbert BC. Kalz W. Lindsay CI. McGrail PT. Parsons AF. Whittaker DTE. J. Chem. Soc., Perkin Trans. 1 2000, 1187

Google Scholar
8g Ikeda M. Teranishi H. Nozaki K. Ishibashi H. J. Chem. Soc., Perkin Trans. 1 1998, 1691

Google Scholar
8h Ozaki S. Matsushita H. Emoto M. Ohmori H. Chem. Pharm. Bull. 1995, 43: 32

Google Scholar
8i Curran DP. Tamine J. J. Org. Chem. 1991, 56: 2746

Google Scholar
9a El Kaïm L. Grimaud L. Miranda LD. Vieu E. Tetrahedron Lett. 2006, 47: 8259

Google Scholar
9b Bertin D. Gigmes D. Marque SRA. Tordo P. Tetrahedron 2005, 61: 8752

Google Scholar
9c Axon J. Boiteau L. Boivin J. Forbes JE. Zard SZ. Tetrahedron Lett. 1994, 35: 1719

Google Scholar
9d Byers JH. Gleason TG. Knight KS. J. Chem. Soc., Chem. Commun. 1991, 355

Google Scholar
For reactions that can be formally considered to belong to the group, see:
9e Cassayre J. Dauge D. Zard SZ. Synlett 2000, 471

Google Scholar
9f Uneyama K. J. Organomet. Chem. 2000, 611: 158

Google Scholar
10a Rowlands GJ. Tetrahedron 2009, 65: 8603

Google Scholar
10b Alcaide B. Almendros P. Luna A. Chem. Rev. 2009, 109: 3817

Google Scholar
10c Clark AJ. Chem. Soc. Rev. 2002, 31: 1

Google Scholar
10d Nagashima H. Itoh K. J. Synth. Org. Chem., Jpn. 1995, 53: 298

Google Scholar
10e Iqbak J. Bathia B. Nayyar NK. Chem. Rev. 1994, 94: 519

Google Scholar
11a Matyjaszewski K. Xia J. Chem. Rev. 2001, 101: 2921

Google Scholar
11b Kamigaito M. Ando T. Sawamoto M. Chem. Rev. 2001, 101: 3689

Google Scholar
11c Poli R. Angew. Chem. Int. Ed. 2006, 45: 5058

Google Scholar
12a Ghelfi F. Pattarozzi M. Roncaglia F. Parsons AF. Felluga F. Pagnoni UM. Valentin E. Mucci A. Bellesia F. Synthesis 2008, 3131

Google Scholar
12b Bull JA. Hutchings MG. Luján C. Quayle P. Tetrahedron Lett. 2008, 49: 1356

Google Scholar
12c Clark AJ. Geden JV. Thom S. J. Org. Chem. 2006, 71: 1471

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

Google Scholar
12e De Buyck L. Danieli C. Ghelfi F. Pagnoni UM. Parsons AF. Pattarozzi M. Roncaglia F. Tetrahedron 2005, 60: 2871

Google Scholar
12f Masahiko I. Masahiko S. Hitoshi N. Hiroshi K. Hiroshi Y. Pest Manag. Sci. 2004, 60: 981

Google Scholar
12g Cagnoli R. Ghelfi F. Pagnoni UM. Parsons AF. Schenetti L. Tetrahedron 2003, 59: 9951

Google Scholar
12h Bryans JS. Chessum NEA. Huther N. Parsons AF. Ghelfi F. Tetrahedron 2003, 59: 6221

Google Scholar
12i Kawano T. Kuwana J. Shinomaru T. Du C.-X. Ueda I. Chem. Lett. 2001, 1230

Google Scholar
12j Clark AJ. Battle GM. Hemings AM. Haddlenton DM. Bridge A. Tetrahedron Lett. 2001, 42: 2003

Google Scholar
12k Nagashima H. Isono Y. Iwamatsu S. J. Org. Chem. 2001, 66: 315

Google Scholar
12l Ghelfi F. Parsons AF. J. Org. Chem. 2000, 65: 6249

Google Scholar
12m Clark AJ. Filik RP. Haddleton DM. Radigue A. Sanders CJ. Thomas GH. Smith ME. J. Org. Chem. 1999, 64: 8954

Google Scholar
12n Clark AJ. Filik RP. Thomas GH. Tetrahedron Lett. 1999, 40: 4885

Google Scholar
12o Iwamatsu S. Kondo H. Matsubara K. Nagashima H. Tetrahedron 1999, 55: 1687

Google Scholar
12p Clark AJ. Duncalf DJ. Filik RP. Haddleton DM. Thomas GH. Wongtap H. Tetrahedron Lett. 1999, 40: 3807

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

Google Scholar
12r Iwamatsu S. Matsubara K. Nagashima H. J. Org. Chem. 1999, 64: 9625

Google Scholar
12s Baldovini N. Bertrand M.-P. Carrière A. Nouguier R. Plancher J.-M. J. Org. Chem. 1996, 61: 3205

Google Scholar
12t Benedetti M. Forti L. Ghelfi F. Pagnoni UM. Ronzoni R. Tetrahedron 1997, 53: 14031

Google Scholar
12u Nagashima H. Ozaki N. Ishii M. Seki K. Washiyama M. Itoh K. J. Org. Chem. 1993, 58: 464

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

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

Google Scholar
14c Motoyama Y. Hanada S. Shimamoto N. Nagashima H. Tetrahedron 2006, 62: 2779

Google Scholar
14d Motoyama Y. Hanada S. Niibayashi S. Shimamoto K. Takaoka N. Nagashima H. Tetrahedron 2005, 61: 10216

Google Scholar
14e Seigal BA. Fajardo C. Snapper ML. J. Am. Chem. Soc. 2005, 127: 16329

Google Scholar
14f Rachita MA. Slough GA. Tetrahedron Lett. 1993, 34: 6821

Google Scholar
14g Ishibashi H. Uemura N. Nakatani H. Okazaki M. Sato T. Nakamura N. Ikeda M. J. Org. Chem. 1993, 58: 2360

Google Scholar
14h Nagashima H. Wakamatsu H. Ozaki N. Ishii T. Watanabe M. Tajima T. Itoh K. J. Org. Chem. 1992, 57: 1682

Google Scholar
15a Braunecker WA. Matyjaszewski K. Prog. Polym. Sci. 2007, 32: 93

Google Scholar
15b Pintauer T. Matyjaszewski K. Chem. Soc. Rev. 2008, 37: 1087

Google Scholar
16a Clark AJ. Tetrahedron Lett. 2008, 49: 4848

Google Scholar
16b Wolf J. Thommes K. Briel O. Scoppelliti R. Severin K. Organometallics 2008, 27: 4464

Google Scholar
16c Thommes K. Içli B. Scoppelliti R. Severin K. Chem. Eur. J. 2007, 13: 6899

Google Scholar
17 Zhu R. Xing L. Wang X. Cheng C. Su D. Hu Y. Adv. Synth. Catal. 2008, 350: 1253

Crossref Google Scholar
18a Bellu D. Pure Appl. Chem. 1985, 57: 1827

Google Scholar
18b Kobrakov KI. Ivanov AV. Chem. Heterocycl. Compd. (Engl. Trans.) 2001, 37: 529

Google Scholar
19a Seijas JA. Vázquez-Tato MP. Castedo L. Estévez RJ. Ónega MG. Ruiz M. Tetrahedron 1992, 48: 1637

Google Scholar
19b Nagashima H. Ozaky N. Seki K. Ishii M. Itoh K. J. Org. Chem. 1989, 54: 4496

Google Scholar
19c Nagashima H. Ara K. Wakamatsu H. Itoh K. J. Chem. Soc., Chem. Commun. 1985, 518

Google Scholar
19d Nagashima H. Wakamatsu H. Itoh K. J. Chem. Soc., Chem. Commun. 1984, 652

Google Scholar
19e Broadhurst MD. inventors; US 4132713.
19f Tseng CK. Teach EG. Simons RW. Synth. Commun. 1984, 14: 1027

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

Google Scholar
20b Channon M. Rajzmann M. Channon F. Tetrahedron 1990, 46: 6193

Google Scholar
20c Timokhin BV. Russ. Chem. Rev. 1990, 59: 193

Google Scholar
21a Muzart J. Tetrahedron 2009, 65: 8313

Google Scholar
21b Karpinets AP. Ukr. Khim. Zh. (Russ. Ed.) 2000, 66: 29 ; Chem. Abstr. 2000, 134, 5189

Google Scholar
21c Khobayashi S. Yasuda M. Hachiya I. Chem. Lett. 1996, 407

Google Scholar
21d Freidlina RK. Chukovskaya EC. Synthesis 1974, 477

Google Scholar