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

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;

Abstract

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

Full Text

References

<A NAME="RP07207SS-1A">1a</A> 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

<A NAME="RP07207SS-1B">1b</A> Saldabol NO. Popelis YuY. Alekseeva LN. Yalynskaya AK. Moskaleva ND. Pharm. Chem. J. (Engl. Transl.) 1977, 11: 790

<A NAME="RP07207SS-1C">1c</A> Saldabol NO. Giller SA. Alekseeva LN. Kruzmetra LV. Pharm. Chem. J. (Engl. Transl.) 1971, 5: 596

<A NAME="RP07207SS-1D">1d</A> Chakrabarti JK. Todd A. Eur. J. Med. Chem. Chim. Ther. 1974, 9: 146

<A NAME="RP07207SS-1E">1e</A> Nishigaki S. Yoneda F. Matsumoto H. Morinaga K. J. Med. Chem. 1969, 12: 39

<A NAME="RP07207SS-1F">1f</A> Gozzo F, Boschi PM, and Longoni A. inventors; DE 2750813. ; Chem. Abstr. 1978, 89, 109506

<A NAME="RP07207SS-1G">1g</A> Kodama H, Takai A, Saikawa I, Matsubara Y, and Hirai S. inventors; JP 1945264. ; Chem. Abstr. 1965, 62, 11822e

<A NAME="RP07207SS-2A">2a</A> 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

<A NAME="RP07207SS-2B">2b</A> 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

<A NAME="RP07207SS-3A">3a</A> Nishigaki S. Ichiba M. Fukazawa S. Kanahori M. Shinomura K. Yoneda F. Senga K. Chem. Pharm. Bull. 1976, 24: 1658

<A NAME="RP07207SS-3B">3b</A> Ziegler HJ. Inion H. Aussems G. Christiaens A. Chaillet F. Charlier R. Chim. Ther. 1971, 6: 159

<A NAME="RP07207SS-3C">3c</A> Saikawa I, Maeda T, Takano S, and Takamichi A. inventors; JP 6824423. ; Chem. Abstr. 1969, 70, 57911x

<A NAME="RP07207SS-3D">3d</A> Miura K. inventors; BE 638221. ; Chem. Abstr. 1965, 62, 7783

<A NAME="RP07207SS-3E">3e</A> Miura K, Ikeda M, Oohashi T, Igarashi Y, and Matsuda S. inventors; DE 1470048. ; Chem. Abstr. 1974, 81, 25677

<A NAME="RP07207SS-3F">3f</A> Saikawa I, and Takano S. inventors; JP 7028162. ; Chem. Abstr. 1971, 74, 3608t

<A NAME="RP07207SS-3G">3g</A> Saikawa I, Maeda T, and Kuroda S. inventors; JP 6827871. ; Chem. Abstr. 1969, 70, 78017a

<A NAME="RP07207SS-4">4</A> Xu G. Hartman TL. Wargo H. Turpin JA. Buckheit RW. Cushman M. Bioorg. Med. Chem. 2002, 10: 283

<A NAME="RP07207SS-5A">5a</A> Boev VI. Moskalenko AI. Russ. J. Gen. Chem. 2000, 70: 413

<A NAME="RP07207SS-5B">5b</A> Yagupol’skii LM. Gruz BE. J. Gen. Chem. USSR (Engl. Transl.) 1961, 31: 3690

<A NAME="RP07207SS-5C">5c</A> Kiprianov AI. Shtets Ya. J. Gen. Chem. USSR (Engl. Transl.) 1963, 33: 3452

<A NAME="RP07207SS-5D">5d</A> Yagupol’skii LM. Gruz BE. Katerinenko LI. J. Gen. Chem. USSR (Engl. Transl.) 1968, 38: 1688

<A NAME="RP07207SS-5E">5e</A> Yagupol’skii LM. Trushanina LI. Il’chenko AYa. J. Org. Chem. USSR (Engl. Transl.) 1975, 11: 2202

<A NAME="RP07207SS-5F">5f</A> Yagupol’skii LM. Gruz BF. J. Gen. Chem. USSR (Engl. Transl.) 1967, 37: 2350

<A NAME="RP07207SS-6A">6a</A> Popov II. Chem. Heterocycl. Compd. (Engl. Transl.) 1997, 33: 949

<A NAME="RP07207SS-6B">6b</A> Cremlyn RJ. Graham S. Saunders D. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 92: 65

<A NAME="RP07207SS-6C">6c</A> Katritzky AR. Lagowski JM. J. Chem. Soc. 1958, 4155

<A NAME="RP07207SS-6D">6d</A> Smith JM. Stewart JHW. Roth B. Northey EH. J. Am. Chem. Soc. 1948, 70: 3997

<A NAME="RP07207SS-6E">6e</A> Loew K. Chem. Ber. 1903, 36: 1666

<A NAME="RP07207SS-6F">6f</A> Fichter F. J. Prakt. Chem. 1906, 74: 320

<A NAME="RP07207SS-7A">7a</A> Prostakov NS. Varlamov AV. Zvolinskii VP. Chem. Heterocycl. Compd. (Engl. Transl.) 1972, 8: 871

<A NAME="RP07207SS-7B">7b</A> Kiprianov AI. Il’chenko Ya. J. Gen. Chem. USSR (Engl. Transl.) 1965, 35: 497

<A NAME="RP07207SS-7C">7c</A> Ruggli P. Cuenin H. Helv. Chim. Acta 1944, 27: 649

<A NAME="RP07207SS-8A">8a</A> 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

<A NAME="RP07207SS-8B">8b</A> Barfoot IMC. Hammick DL. Morgan ED. Roe AM. J. Chem. Soc. 1957, 1533

<A NAME="RP07207SS-9A">9a</A> Shvartsberg MS. Ivanchikova ID. Fedenok LG. Tetrahedron Lett. 1994, 35: 6749

<A NAME="RP07207SS-9B">9b</A> Shvartsberg MS. Ivanchikova ID. Fedenok LG. Russ. Chem. Bull. 1996, 45: 1714

<A NAME="RP07207SS-9C">9c</A> Fedenok LG. Barabanov II. Ivanchikova ID. Tetrahedron Lett. 1999, 40: 805

<A NAME="RP07207SS-9D">9d</A> Shvekhgeimer M.-GA. Kartseva OS. Kobrakov KI. Popandopulo NG. Chem. Heterocycl. Compd. (Engl. Transl.) 1993, 29: 339

<A NAME="RP07207SS-9E">9e</A> Hagmann WK. Basha FZ. Hashimoto M. Frye BR. Kojo S. Hecht SM. J. Org. Chem. 1981, 46: 1413

<A NAME="RP07207SS-10A">10a</A> Katagiri N. Takashima K. Kato T. Sato S. Tamura C. J. Chem. Soc., Perkin Trans. 1 1983, 201

<A NAME="RP07207SS-10B">10b</A> Konno S. Sato Y. Sakamoto T. Katagiri N. Yamanaka H. Heterocycles 1984, 22: 1331

<A NAME="RP07207SS-10C">10c</A> Gonzales J. Perez-Medrano A. Muchowski JM. Can. J. Chem. 1997, 75: 1409

<A NAME="RP07207SS-11">11</A> Chen C. Wilcoxen K. Zhu Y.-F. Kim K. McCarthy JR. J. Org. Chem. 1999, 64: 3476

<A NAME="RP07207SS-12">12</A> Liron F. Gervais M. Peyrat J.-F. Alami M. Brion J.-D. Tetrahedron Lett. 2003, 44: 2789

<A NAME="RP07207SS-13">13</A> Shi J. Negishi E. J. Organomet. Chem. 2003, 687: 518

<A NAME="RP07207SS-14A">14a</A> Dubey PK. Kumar R. Grossert JS. Hooper DL. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1999, 38: 1041

<A NAME="RP07207SS-14B">14b</A> Saldabol NO. Popelis YuY. Chem. Heterocycl. Compd. (Engl. Transl.) 1977, 13: 246

<A NAME="RP07207SS-14C">14c</A> Saldabol NO. Popelis YuY. Chem. Heterocycl. Compd. (Engl. Transl.) 1977, 13: 451

<A NAME="RP07207SS-14D">14d</A> Saldabol NO. Zeligman LL. Giller SA. Chem. Heterocycl. Compd. (Engl. Transl.) 1973, 9: 126

<A NAME="RP07207SS-15A">15a</A> Vikrishchuk NI. Suzdalev KF. Ryabukhin YuI. Zhdanov YuA. Russ. J. Org. Chem. 1998, 34: 564

<A NAME="RP07207SS-15B">15b</A> Capriati V. Florio S. Luisi R. Eur. J. Org. Chem. 2001, 2035

<A NAME="RP07207SS-16">16</A> Florio S. Troisi L. Capriati V. Coletta G. Tetrahedron 1999, 55: 9859

<A NAME="RP07207SS-17">17</A> Ryabukhin SV. Plaskon AS. Tverdokhlebov AV. Tolmachev AA. Synth. Commun. 2004, 34: 1483

<A NAME="RP07207SS-18A">18a</A> Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synlett 2004, 2287

<A NAME="RP07207SS-18B">18b</A> Tereshchenko AD. Sysoev DA. Tverdokhlebov AV. Tolmachev AA. Synthesis 2006, 349

<A NAME="RP07207SS-18C">18c</A> Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis 2006, 3715

<A NAME="RP07207SS-18D">18d</A> Ryabukhin SV. Plaskon AS. Ostapchuk EN. Volochnyuk DM. Tolmachev AA. Synthesis 2007, 417

<A NAME="RP07207SS-19A">19a</A> Zhu Y.-L. Huang S.-L. Pan Y.-J. Eur. J. Org. Chem. 2005, 2354

<A NAME="RP07207SS-19B">19b</A> Zhu Y.-L. Pan Y.-J. Huang S.-L. Synth. Commun. 2004, 34: 3167

<A NAME="RP07207SS-19C">19c</A> Zhu Y.-L. Pan Y.-J. Huang S.-L. Heterocycles 2005, 65: 133

<A NAME="RP07207SS-19D">19d</A> Saidi MR. Azizi N. Tetrahedron: Asymmetry 2002, 13: 2523

<A NAME="RP07207SS-19E">19e</A> Saidi MR. Azizi N. Synlett 2002, 1347

<A NAME="RP07207SS-19F">19f</A> Bolognesi ML. Andrisano V. Bartolini M. Minarini A. Rosini M. Tumiatti V. Melchiorre C. J. Med. Chem. 2001, 44: 105

<A NAME="RP07207SS-19G">19g</A> Zavyalov SI. Kulikova LB. Khim.-Farm. Zh. 1992, 26: 116

<A NAME="RP07207SS-20">20</A> Sabitha G. Reddy GSKK. Reddy CS. Yadav JS. Synlett 2003, 858

<A NAME="RP07207SS-21A">21a</A> Alphonse F.-A. Suzenet F. Keromnes A. Lebret B. Guillaumet G. Org. Lett. 2003, 5: 803

<A NAME="RP07207SS-21B">21b</A> Hellwinkel D. Goeke K. Karle R. Synthesis 1994, 973

<A NAME="RP07207SS-21C">21c</A> Cuadro A. Perez-Butragueno J. Pastor-Maeso M. Alvarez-Builla J. Martinez-Grueiro MM. Martinez-Fernandez AR. Farmaco 1992, 47: 477

<A NAME="RP07207SS-21D">21d</A> Chakraborti AK. Rudrawar S. Kaur G. Sharma L. Synlett 2004, 1533