A Facile Atom-Economic Synthesis
of Imidazoles with Chalcogenophosphoryl Substituents via Free-Radical
Addition of Secondary Phosphine Chalcogenides to 1-Vinylimidazoles

Nina K. Gusarova; Svetlana F. Malysheva; Nataliya A. Belogorlova; Lidiya N. Parshina; Boris A. Trofimov

doi:10.1055/s-0030-1260025

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 Linkedin Weibo

Download PDF

Synthesis 2011(11): 1777-1782
DOI: 10.1055/s-0030-1260025

PAPER

A Facile Atom-Economic Synthesis of Imidazoles with Chalcogenophosphoryl Substituents via Free-Radical Addition of Secondary Phosphine Chalcogenides to 1-Vinylimidazoles

Nina K. Gusarova, Svetlana F. Malysheva, Nataliya A. Belogorlova, Lidiya N. Parshina, Boris A. Trofimov*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, 664033 Irkutsk, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;

Further Information

Publication History

Received 13 February 2011
Publication Date:
05 May 2011 (online)

Abstract
Full Text
References

Buy Article Permissions and Reprints All articles of this category

Abstract

Secondary phosphine sulfides and selenides react with 1-vinylimidazoles under radical initiation conditions to give the corresponding anti-Markovnikov adducts in up to 98% yields.

Key words

1-vinylimidazoles - phosphine sulfides - phosphine selenides - radical addition

References

1a Grimmett MR. In Comprehensive Heterocyclic Chemistry II Vol. 3: Katritzky AR. Rees CW. Scriven EFV. Pergamon; Oxford: 1996. p.77-220

Search in Google Scholar
1b Hoffmann H. Lindel T. Synthesis 2003, 1753
1c De Luca L. Curr. Med. Chem. 2006, 13: 1

Search in Google Scholar
1d Jin Z. Nat. Prod. Rep. 2006, 23: 464

Search in Google Scholar
1e Sivappa R. Hernandez NM. He Y. Lovely CJ. Org. Lett. 2007, 9: 3861

Search in Google Scholar
1f Bellina F. Cauteruccio S. Rossi R. Tetrahedron 2007, 63: 4571

Search in Google Scholar
2a Welton T. Chem. Rev. 1999, 99: 2071

Search in Google Scholar
2b Wasserscheid P. Keim W. Angew. Chem. Int. Ed. 2000, 39: 3772

Search in Google Scholar
2c Forsyth SA. Pringle JM. MacFarlane DR. Aust. J. Chem. 2004, 57: 113

Search in Google Scholar
2d Chiappe C. Pieraccini D. J. Phys. Org. Chem. 2005, 18: 275

Search in Google Scholar
2e Rahman T. Fukuyama T. Ryu I. Suzuki K. Yonemura K. Hughes PF. Nokihara K. Tetrahedron Lett. 2006, 47: 2703

Search in Google Scholar
2f Xu J.-M. Liu B.-K. Wu W.-B. Qian C. Wu Q. Lin X.-F. J. Org. Chem. 2006, 71: 3991

Search in Google Scholar
2g Greaves TL. Drummond CJ. Chem. Rev. 2008, 108: 206

Search in Google Scholar
2h Plaquevent J.-C. Levillain J. Guillen F. Malhiac C. Gaumont A.-C. Chem. Rev. 2008, 108: 5035

Search in Google Scholar
3a Ding H. Ma C. Yang Y. Wang Y. Org. Lett. 2005, 7: 2125

Search in Google Scholar
3b Pathan MY. Paike VV. Pachmase PR. More SP. Ardhapure SS. Pawar RP. ARKIVOC 2006, (xv): 205

Search in Google Scholar
4a Jalil MA. Yamada T. Fujinami S. Hojo T. Nishikawa H. Polyhedron 2001, 20: 627

Search in Google Scholar
4b Grotjahn DB. Incarvito CD. Rheingold AL. Angew. Chem. Int. Ed. 2001, 40: 3884

Search in Google Scholar
4c Harkal S. Rataboul F. Zapf A. Fuhrmann C. Riermeier T. Monsees A. Beller M. Adv. Synth. Catal. 2004, 346: 1742

Search in Google Scholar
4d Grotjahn DB. Gong Y. Zakharov L. Golen JA. Rheingold AL. J. Am. Chem. Soc. 2006, 128: 438

Search in Google Scholar
4e Debono N. Canac Y. Duhayon C. Chauvin R. Eur. J. Inorg. Chem. 2008, 2991
4f Canac Y. Debono N. Vendier L. Chauvin R. Inorg. Chem. 2009, 48: 5562

Search in Google Scholar
4g Schulz T. Torborg C. Schäffner B. Huang J. Zapf A. Kadyrov R. Börner A. Beller M. Angew. Chem. Int. Ed. 2009, 48: 918 ; Angew. Chem. 2009, 121, 936

Search in Google Scholar
4h Field LD. Messerle BA. Vuong KQ. Turner P. Dalton Trans. 2009, 3599
5 Trofimov BA. Malysheva SF. Parshina LN. Gusarova NK. Belogorlova NA. Synlett 2011, 94

Thieme Connect
6a Gusarova NK. Bogdanova MV. Ivanova NI. Chernysheva NA. Sukhov BG. Sinegovskaya LM. Kazheva ON. Alexandrov GG. D’yachenko OA. Trofimov BA. Synthesis 2005, 3103
6b Sukhov BG. Gusarova NK. Ivanova NI. Bogdanova MV. Kazheva ON. Alexandrov GG. D’yachenko OA. Sinegovskaya LM. Malysheva SF. Trofimov BA.
J. Struct. Chem. 2005, 46: 1066

Search in Google Scholar
6c Gusarova NK. Malysheva SF. Kuimov VA. Belogorlova NA. Mikhailenko VL. Trofimov BA. Mendeleev Commun. 2008, 18: 260

Search in Google Scholar
6d Trofimov BA. Gusarova NK. Mendeleev Commun. 2009, 19: 295

Search in Google Scholar
6e Malysheva SF. Artem’ev AV. Gusarova NK. Timokhin BV. Tatarinova AA. Trofimov BA. Russ. J. Gen. Chem. 2009, 79: 1617

Search in Google Scholar
6f Gusarova NK. Malysheva SF. Belogorlova NA. Kazheva ON. Chekhlov AN. Alexandrov GG. D’yachenko OA. Sinegovskaya LM. Trofimov BA. J. Struct. Chem. 2010, 51: 120

Search in Google Scholar
7a Leca D. Fensterbank L. Lacôte E. Malakria M. Chem. Soc. Rev. 2005, 34: 858

Search in Google Scholar
7b Coudray L. Montchamp J.-L. Eur. J. Org. Chem. 2008, 3601
7c Trofimov BA. Gusarova NK. Chernysheva NA. Yas’ko SV. Kazantseva TI. Ushakov IA. Synthesis 2008, 2743
8 Jessop CM. Parsons AF. Routledge A. Irvine DJ. Eur. J. Org. Chem. 2006, 1547
9a Gusarova NK. Malysheva SF. Oparina LA. Belogorlova NA. Tantsyrev AP. Parshina LN. Sukhov BG. Tlegenov RT. Trofimov BA. ARKIVOC 2009, (vii): 260

Search in Google Scholar
9b Oparina LA. Malysheva SF. Gusarova NK. Vysotskaya OV. Stepanov AV. Belogorlova NA. Albanov AI. Trofimov BA. Synthesis 2009, 3427
10a Shostakovskii MF. Skvortsova GG. Glazkova NP. Domnina ES. Chem. Heterocycl. Compd. 1969, 1070
10b Mamashvili TN. Keiko NA. Kalikhman ID. Domnina ES. Glazkova NP. Voronkov MG. Russ. Chem. Bull. 1987, 2122