A Facile and Practical Solvent-Free
One-Pot Synthesis of (Z)-4-Methylene-3-selenaquinoline
Derivatives from o-Ethynylanilines and
Isoselenocyanates

Haruki Sashida; Chao Pan; Mamoru Kaname; Mao Minoura

doi:10.1055/s-0030-1258171

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Synthesis 2010(18): 3091-3096
DOI: 10.1055/s-0030-1258171

PAPER

A Facile and Practical Solvent-Free One-Pot Synthesis of (Z)-4-Methylene-3-selenaquinoline Derivatives from o-Ethynylanilines and Isoselenocyanates [¹]

Haruki Sashida*^a, Chao Pan^a, Mamoru Kaname^a, Mao Minoura^b
^a Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
e-Mail: h-sashida@hokuriku-u.ac.jp;
^b Department of Chemistry, School of Science, Kitasato University, 1-15-1 Kitasato, minami-ku, Sagamihara, Kanagawa 252-0373, Japan

Further Information

Publication History

Received 20 April 2010
Publication Date:
12 July 2010 (online)

Abstract
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Abstract

Heating of o-ethynylanilines with isoselenocyanates directly resulted in the 6-exo-dig mode ring-closure reaction of the adducts to give the (Z)-2-imino-4-methylene-3-selenaquinolines in moderate to good yields. Based on this convenient, solvent-free, catalyst-free method, several 3-selenaquinoline derivatives (3,1-benzoselenazines) were easily obtained in one pot. Successful application of the microwave-assisted synthesis of these compounds was also investigated.

Key words

o-ethynyaniline - isoselenocyanate - 3-selenaquinoline - 6-exo mode cyclization - microwave

References

1 This paper constitutes Part 31 in the series ‘Studies on Tellurium-Containing Heterocycles’, For Part 30, see: Sashida H. Kaname M. Nakayama A. Suzuki H. Minoura M. Tetrahedron 2010, 66: 5149

Crossref Google Scholar
2a Selenium in Biology and Medicine Wengel A. Springer; Berlin: 1989.

Google Scholar
2b Burk RF. Selenium in Biology and Human Health Springer; New York: 1994.

Google Scholar
2c Xu Y. Kool ET. J. Am. Chem. Soc. 2000, 122: 9040

Google Scholar
2d Mugesh G. du Mont W.-W. Sies H. Chem. Rev. 2001, 101: 2125

Google Scholar
2e Soriano-Garcia M. Curr. Med. Chem. 2004, 11: 1657

Google Scholar
3 Koketsu M. Ishihara H. Curr. Org. Chem. 2003, 7: 175

Crossref Google Scholar
4a Koketsu M. Tanaka Y. Hiramatsu S. Ishihara H. Heterocycles 2001, 55: 1181

Google Scholar
4b Koketsu M. Senda T. Hiramatsu S. Ishihara H. J. Chem. Soc., Perkin Trans. 1 1999, 453

Google Scholar
4c Koketsu M. Hiramatsu S. Ishihara H. Chem. Lett. 1999, 485

Google Scholar
4d Bochu C. Couture A. Grandelaudon P. J. Org. Chem. 1988, 53: 4852

Google Scholar
4e Dubreuil D. Pradere JP. Giraudeau N. Goli M. Tonnard F. Tetrahedron Lett. 1995, 36: 237

Google Scholar
4f Sekiguchi M. Ogawa A. Fujiwara S. Ryu I. Kambe N. Sonoda N. Chem. Lett. 1990, 913

Google Scholar
4g Shimada K. Akikawa K. Fujita T. Aoyagi S. Takikawa Y. Kabuto C. Chem. Lett. 1997, 701

Google Scholar
5a Takahashi M. Watanabe S. Kasai T. Heterocycles 1980, 14: 1921

Google Scholar
5b Liebscher J. Hartmann H. Tetrahedron Lett. 1976, 17: 2005

Google Scholar
6 Yokoyama M. Kumada K. Hatanaka H. Shiraishi T. Bull. Chem. Soc. Jpn. 1986, 48: 1613

Google Scholar
7a Simchen G. Angew. Chem., Int. Ed. Engl. 1968, 7: 464

Google Scholar
7b Simchen G. Wenzelburger J. Chem. Ber. 1970, 103: 413

Google Scholar
7c Simchen G. Entenmann G. Angew. Chem., Int. Ed. Engl. 1973, 12: 119

Google Scholar
8 Garud DR. Koketsu M. Ishihara H. Molecules 2007, 12: 504

Crossref PubMed Google Scholar
9 Toyada Y. Garuda DR. Koketsu M. Heterocycles 2009, 78: 449

Crossref Google Scholar
10 Garud DR. Toyoda Y. Koketsu M. Tetrahedron Lett. 2009, 50: 3035

Crossref Google Scholar
11 Sommen GL. Linden A. Heimgartner H. Tetrahedron Lett. 2005, 46: 6723

Crossref Google Scholar
12 Koketsu M. Sakai T. Kiyokuni T. Garuda DR. Ando H. Ishihara H. Heterocycles 2006, 68: 1604

Google Scholar
13 Sommen GL. Linden A. Heimgartner H. Tetrahedron 2006, 62: 3344

Crossref Google Scholar
14 Ye S. Ding Q. Wang Z. Zhou H. Wu J. Org. Biomol. Chem. 2008, 6: 4406

Crossref Google Scholar
15 Ding Q. Wu J. J. Comb. Chem. 2008, 10: 541

Crossref Google Scholar
16a Sashida H. Rev. Heteroat. Chem. 2000, 22: 59

Google Scholar
16b Sashida H. J. Synth. Org. Chem. Jpn. 2001, 59: 355

Google Scholar
17 Sashida H. Nakayama A. Kaname M. Synthesis 2008, 3229

Article in Thieme Connect Google Scholar
18 Martins MAP. Frizzo CP. Moreira DN. Buriol L. Machado P. Chem. Rev. 2009, 109: 4140

Crossref Google Scholar
19a Lidström P. Tierney J. Wathey B. Westman J. Tetrahedron 2001, 57: 9225

Google Scholar
19b Xu Y. Guo Q.-X. Heterocycles 2004, 63: 903

Google Scholar
19c Jindal R. Bajaj S. Curr. Org. Chem. 2008, 12: 836

Google Scholar
19d Hugel HM. Molecules 2009, 14: 4936

Google Scholar
21 Shi C. Zhang Q. Wang K. J. Org. Chem. 1999, 64: 925

Crossref PubMed Google Scholar
22 Koradin C. Dohle W. Rodrigues A. Schmid B. Knochel P. Tetrahedron 2003, 59: 157

Google Scholar
23 Woodgate PD. Sutherland H. J. Organomet. Chem. 2001, 629: 131

Crossref Google Scholar
24 Villemin D. Goussu D. Heterocycles 1989, 29: 1255

Google Scholar
25 Sonoda N. Yamamoto G. Tsutsumi S. Bull Chem. Soc. Jpn. 1972, 45: 2937

Crossref Google Scholar
26 Fernändes-Bolaños JG. López . Ulgar V. Maya I. Fuentes J. Tetrahedron Lett. 2004, 45: 4081

Crossref Google Scholar

20

Single crystals of 3Dd were obtained from solns of CHCl₃ after slow evaporation of the solvent at r.t. Diffraction data were collected on a Bruker Apex-II CCD. The structure analysis is based on 2629 observed reflections with I > 2.00σ(I) and 217 variable parameters; colorless prisms, C₂₁H₁₆N₂Se, FW = 375.32, 233 K, monoclinic, space group P2₁/n, a = 10.3882(7) Å, b = 8.3928(5) Å, c = 19.432(1) Å, β = 91.164(1)˚, V = 1693.9(2) Å^³, Z = 4, R = 0.0288, R _w = 0.0759, GOF = 1.037. The supplementary crystallographic data for 3Dd (CCDC-773220) can be obtained free of charge from the Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/products/csd/request/request.php4.