Chlorotrimethylsilane-Mediated Synthesis of 2-Aryl-1-chloro-1-heteroarylalkenes

Sergey V. Ryabukhin; Andrey S. Plaskon; Dmitriy M. Volochnyuk; Andrey A. Tolmachev

doi:10.1055/s-2007-990791

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 2007(20): 3163-3170
DOI: 10.1055/s-2007-990791

PAPER

Chlorotrimethylsilane-Mediated Synthesis of 2-Aryl-1-chloro-1-heteroarylalkenes

Sergey V. Ryabukhin^a,b, Andrey S. Plaskon^a,b, Dmitriy M. Volochnyuk*^a,c, Andrey A. Tolmachev^b
^a Enamine Ltd., 23 Alexandra Matrosova st., 01103 Kiev, Ukraine
^b National Taras Shevchenko University, 62 Volodymyrska st., 01033 Kiev, Ukraine
^c Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Murmanska 5, 02094 Kiev, Ukraine
Fax: +380(44)5373253; e-Mail: D.Volochnyuk@enamine.net;

Further Information

Publication History

Received 3 June 2007
Publication Date:
21 September 2007 (online)

Abstract
Full Text
References

Permissions and Reprints All articles of this category

Abstract

The condensation of (chloromethyl)heterarenes with aromatic aldehydes was investigated, resulting in a simple and flexible general procedure for the synthesis of 2-aryl-1-chloro-1-heteroarylalkenes. The best reaction conditions were found to be heating in N,N-dimethylformamide in the presence of chlorotrimethylsilane as a promoter and water-scavenger.

Key words

(chloromethyl)heterocycles - aromatic aldehydes - Knoevenagel condensation - 2-aryl-1-halo-1-heteroarylalkene - chlorotrimethylsilane

References

1a Gopalsamy A. Lim K. Ellingboe JW. Mitsner B. Nikitenko A. Upeslacis J. Mansour TS. Olson MW. Bebernitz GA. Grinberg D. Feld B. Moy FJ. O’Connell J. J. Med. Chem. 2004, 47: 1893

Crossref Search in Google Scholar
1b Saldabol NO. Popelis YuY. Alekseeva LN. Yalynskaya AK. Moskaleva ND. Pharm. Chem. J. (Engl. Transl.) 1977, 11: 790

Crossref Search in Google Scholar
1c Saldabol NO. Giller SA. Alekseeva LN. Kruzmetra LV. Pharm. Chem. J. (Engl. Transl.) 1971, 5: 596

Crossref Search in Google Scholar
1d Chakrabarti JK. Todd A. Eur. J. Med. Chem. Chim. Ther. 1974, 9: 146

Crossref Search in Google Scholar
1e Nishigaki S. Yoneda F. Matsumoto H. Morinaga K. J. Med. Chem. 1969, 12: 39

Crossref Search in Google Scholar
1f Gozzo F, Boschi PM, and Longoni A. inventors; DE 2750813. ; Chem. Abstr. 1978, 89, 109506

Crossref
1g Kodama H, Takai A, Saikawa I, Matsubara Y, and Hirai S. inventors; JP 1945264. ; Chem. Abstr. 1965, 62, 11822e

Crossref
2a Sciotti RJ. Pliushchev M. Wiedeman PE. Balli D. Flamm R. Nilius AM. Marsh K. Stolarik D. Jolly R. Ulrich R. Djuric SW. Bioorg. Med. Chem. Lett. 2002, 12: 2121

Crossref Search in Google Scholar
2b Jacobson KA. Gallo-Rodriguez C. Melman N. Fischer B. Maillard M. van Bergen A. van Galen FJM. Karton Y. J. Med. Chem. 1993, 36: 1333

Crossref Search in Google Scholar
3a Nishigaki S. Ichiba M. Fukazawa S. Kanahori M. Shinomura K. Yoneda F. Senga K. Chem. Pharm. Bull. 1976, 24: 1658

Search in Google Scholar
3b Ziegler HJ. Inion H. Aussems G. Christiaens A. Chaillet F. Charlier R. Chim. Ther. 1971, 6: 159

Search in Google Scholar
3c Saikawa I, Maeda T, Takano S, and Takamichi A. inventors; JP 6824423. ; Chem. Abstr. 1969, 70, 57911x
3d Miura K. inventors; BE 638221. ; Chem. Abstr. 1965, 62, 7783
3e Miura K, Ikeda M, Oohashi T, Igarashi Y, and Matsuda S. inventors; DE 1470048. ; Chem. Abstr. 1974, 81, 25677
3f Saikawa I, and Takano S. inventors; JP 7028162. ; Chem. Abstr. 1971, 74, 3608t
3g Saikawa I, Maeda T, and Kuroda S. inventors; JP 6827871. ; Chem. Abstr. 1969, 70, 78017a
4 Xu G. Hartman TL. Wargo H. Turpin JA. Buckheit RW. Cushman M. Bioorg. Med. Chem. 2002, 10: 283

Crossref Search in Google Scholar
5a Boev VI. Moskalenko AI. Russ. J. Gen. Chem. 2000, 70: 413

Search in Google Scholar
5b Yagupol’skii LM. Gruz BE. J. Gen. Chem. USSR (Engl. Transl.) 1961, 31: 3690

Search in Google Scholar
5c Kiprianov AI. Shtets Ya. J. Gen. Chem. USSR (Engl. Transl.) 1963, 33: 3452

Search in Google Scholar
5d Yagupol’skii LM. Gruz BE. Katerinenko LI. J. Gen. Chem. USSR (Engl. Transl.) 1968, 38: 1688

Search in Google Scholar
5e Yagupol’skii LM. Trushanina LI. Il’chenko AYa. J. Org. Chem. USSR (Engl. Transl.) 1975, 11: 2202

Search in Google Scholar
5f Yagupol’skii LM. Gruz BF. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37: 2350

Search in Google Scholar
6a Popov II. Chem. Heterocycl. Compd. (Engl. Transl.) 1997, 33: 949

Search in Google Scholar
6b Cremlyn RJ. Graham S. Saunders D. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 92: 65

Search in Google Scholar
6c Katritzky AR. Lagowski JM. J. Chem. Soc. 1958, 4155
6d Smith JM. Stewart JHW. Roth B. Northey EH. J. Am. Chem. Soc. 1948, 70: 3997

Search in Google Scholar
6e Loew K. Chem. Ber. 1903, 36: 1666

Search in Google Scholar
6f Fichter F. J. Prakt. Chem. 1906, 74: 320

Search in Google Scholar
7a Prostakov NS. Varlamov AV. Zvolinskii VP. Chem. Heterocycl. Compd. (Engl. Transl.) 1972, 8: 871

Crossref Search in Google Scholar
7b Kiprianov AI. Il’chenko Ya. J. Gen. Chem. USSR (Engl. Transl.) 1965, 35: 497

Crossref Search in Google Scholar
7c Ruggli P. Cuenin H. Helv. Chim. Acta 1944, 27: 649

Crossref Search in Google Scholar
8a Lin C.-F. Duh T.-H. Lu W.-D. Lee J.-L. Lee C.-Y. Chen C.-C. Wu M.-J. J. Chin. Chem. Soc. (Taipei) 2004, 51: 183

Search in Google Scholar
8b Barfoot IMC. Hammick DL. Morgan ED. Roe AM. J. Chem. Soc. 1957, 1533
9a Shvartsberg MS. Ivanchikova ID. Fedenok LG. Tetrahedron Lett. 1994, 35: 6749

Crossref Search in Google Scholar
9b Shvartsberg MS. Ivanchikova ID. Fedenok LG. Russ. Chem. Bull. 1996, 45: 1714

Crossref Search in Google Scholar
9c Fedenok LG. Barabanov II. Ivanchikova ID. Tetrahedron Lett. 1999, 40: 805

Crossref Search in Google Scholar
9d Shvekhgeimer M.-GA. Kartseva OS. Kobrakov KI. Popandopulo NG. Chem. Heterocycl. Compd. (Engl. Transl.) 1993, 29: 339

Crossref Search in Google Scholar
9e Hagmann WK. Basha FZ. Hashimoto M. Frye BR. Kojo S. Hecht SM. J. Org. Chem. 1981, 46: 1413

Crossref Search in Google Scholar
10a Katagiri N. Takashima K. Kato T. Sato S. Tamura C. J. Chem. Soc., Perkin Trans. 1 1983, 201

Crossref
10b Konno S. Sato Y. Sakamoto T. Katagiri N. Yamanaka H. Heterocycles 1984, 22: 1331

Crossref Search in Google Scholar
10c Gonzales J. Perez-Medrano A. Muchowski JM. Can. J. Chem. 1997, 75: 1409

Crossref Search in Google Scholar
11 Chen C. Wilcoxen K. Zhu Y.-F. Kim K. McCarthy JR. J. Org. Chem. 1999, 64: 3476

Crossref Search in Google Scholar
12 Liron F. Gervais M. Peyrat J.-F. Alami M. Brion J.-D. Tetrahedron Lett. 2003, 44: 2789

Crossref Search in Google Scholar
13 Shi J. Negishi E. J. Organomet. Chem. 2003, 687: 518

Crossref Search in Google Scholar
14a Dubey PK. Kumar R. Grossert JS. Hooper DL. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999, 38: 1041

Crossref Search in Google Scholar
14b Saldabol NO. Popelis YuY. Chem. Heterocycl. Compd. (Engl. Transl.) 1977, 13: 246

Crossref Search in Google Scholar
14c Saldabol NO. Popelis YuY. Chem. Heterocycl. Compd. (Engl. Transl.) 1977, 13: 451

Crossref Search in Google Scholar
14d Saldabol NO. Zeligman LL. Giller SA. Chem. Heterocycl. Compd. (Engl. Transl.) 1973, 9: 126

Crossref Search in Google Scholar
15a Vikrishchuk NI. Suzdalev KF. Ryabukhin YuI. Zhdanov YuA. Russ. J. Org. Chem. 1998, 34: 564

Crossref Search in Google Scholar
15b Capriati V. Florio S. Luisi R. Eur. J. Org. Chem. 2001, 2035

Crossref
16 Florio S. Troisi L. Capriati V. Coletta G. Tetrahedron 1999, 55: 9859

Crossref Search in Google Scholar
17 Ryabukhin SV. Plaskon AS. Tverdokhlebov AV. Tolmachev AA. Synth. Commun. 2004, 34: 1483

Crossref Search in Google Scholar
18a Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synlett 2004, 2287

Thieme Connect
18b Tereshchenko AD. Sysoev DA. Tverdokhlebov AV. Tolmachev AA. Synthesis 2006, 349

Thieme Connect
18c Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis 2006, 3715

Thieme Connect
18d Ryabukhin SV. Plaskon AS. Ostapchuk EN. Volochnyuk DM. Tolmachev AA. Synthesis 2007, 417

Thieme Connect
19a Zhu Y.-L. Huang S.-L. Pan Y.-J. Eur. J. Org. Chem. 2005, 2354
19b Zhu Y.-L. Pan Y.-J. Huang S.-L. Synth. Commun. 2004, 34: 3167

Search in Google Scholar
19c Zhu Y.-L. Pan Y.-J. Huang S.-L. Heterocycles 2005, 65: 133

Search in Google Scholar
19d Saidi MR. Azizi N. Tetrahedron: Asymmetry 2002, 13: 2523

Search in Google Scholar
19e Saidi MR. Azizi N. Synlett 2002, 1347
19f Bolognesi ML. Andrisano V. Bartolini M. Minarini A. Rosini M. Tumiatti V. Melchiorre C. J. Med. Chem. 2001, 44: 105

Search in Google Scholar
19g Zavyalov SI. Kulikova LB. Khim.-Farm. Zh. 1992, 26: 116

Search in Google Scholar
20 Sabitha G. Reddy GSKK. Reddy CS. Yadav JS. Synlett 2003, 858

Thieme Connect
21a Alphonse F.-A. Suzenet F. Keromnes A. Lebret B. Guillaumet G. Org. Lett. 2003, 5: 803

Thieme Connect Search in Google Scholar
21b Hellwinkel D. Goeke K. Karle R. Synthesis 1994, 973

Thieme Connect
21c Cuadro A. Perez-Butragueno J. Pastor-Maeso M. Alvarez-Builla J. Martinez-Grueiro MM. Martinez-Fernandez AR. Farmaco 1992, 47: 477

Thieme Connect Search in Google Scholar
21d Chakraborti AK. Rudrawar S. Kaur G. Sharma L. Synlett 2004, 1533

Thieme Connect