Abstract
1,3,5-Trisubstituted-2-pyrazolines were effectively synthesised by utilising chlorotrimethylsilane as an efficient promoter in the cyclisation addition of phenylhydrazine to chalcones under nitrogen in acetonitrile. The clean, mild reaction conditions, high yields and a simple workup of target compounds were attractive features of the reaction which enables a facile preparative procedure for building the pyrazoline ring.
References
1.
Gilchrist T.L.
, Heterocyclic chemistry , 3rd edn., Addison-Wesly , Longman, Ltd , 1998 .
2.
Lednicer D.
, Strategies for Organic Drugs Synthesis and Design , Wiley & Sons : New York , 1998 .
3.
Kozikowski A.P.
, Acct. Chem. Res. , 1984 , 17 , 410 .
4.
Goodell J.R.
,
Puig-Basagoiti F.
,
Forshey B.M.
,
Shi P.-Y.
, and
Ferguson D.M.
, J. Med. Chem. , 2006 , 49 , 2127 .
5.
Frigola J.
,
Colombo A.
,
Pares J.
,
Martinez L.
,
Sagarra R.
, and
Roster R.
, Eur. J. Med. Chem. , 1989 , 24 , 435 .
6.
Copp F.C.
,
Islip P.J.
, and
Tateson J.E.
, Biochem. Pharmacol. , 1984 , 33 , 339 .
7.
Rao N.S.
, and
Rao J.T.
, Asian J. Chem. , 2004 , 16 , 1959 .
8.
Parmer S.S.
,
Pandey B.R.
,
Dwivedi C.
, and
Harbison R.D.
, J. Pharm. Sci. , 1974 , 63 , 1152 .
9.
Takabata E.
,
Kodama R.
,
Dohmori R.
,
Tachizawa H.
, and
Naito T.
, Chem. Pharm. Bull. , 1979 , 16 , 1900 .
10.
Soni N.
,
Pande K.
,
Kalsi R.
,
Gupta T.K.
,
Parmer S.S.
, and
Barthwal J.P.
, Res. Commun. Chem. Pathol. Pharmacol. , 1987 , 56 , 129 .
11.
Groutas W.C.
,
Venkataman R.
,
Chong L.S.
,
Yoder J.E.
,
Epp J.B.
,
Stanga M.A.
, and
Kim E.
, Bioorg. Med. Chem. , 1995 , 3 , 125 .
12.
Klimova E.I.
,
Marcos M.
,
Klimova T.B.
,
Ceeilio A.T.
,
Ruben A.T.
, and
Lran R.R.
, J. Organomet. Chem. , 1999 , 106 , 585 .
13.
Padmavathi V.
,
Sumathi R.P.
,
Chandrasekhar B.N.
, and
Bhaskarreddy D.
, J. Chem. Res. , 1999 , 6101 .
14.
Guerra F.M.
,
Mish M.R.
, and
Carreira E.M.
, Org. Lett. , 2000 , 2 , 4265 .
15.
Whitlock G.A.
, and
Carreira E.M.
, J. Org. Chem. , 1997 , 62 , 7916 .
16.
Whitlock G.A.
, and
Carreira E.M.
, Helv. Chim. Acta , 2000 , 23 , 2007 .
17.
Yaron A.
, and
Naider F.
, Crit. Rev. Biochem. Mol. Biol. , 1993 , 28 , 31 .
18.
Eberhardt E.S.
,
Panasik N.
, and
Raines R.T.
, J. Am. Chem. Soc. , 1996 , 118 , 12261 .
19.
Beausoleil E.
,
L'Archveque B.
,
Belec L.
,
Aftani M.
, and
Lubell W.D.
, J. Org. Chem. , 1996 , 61 , 9447 .
20.
Dummy P.
,
Keller M.
,
Ryan D.E.
,
Rohwedder P.
,
Wohr T.
, and
Mutter M.
, J. Am. Chem. Soc. , 1997 , 119 , 918 .
21.
Travins J.M.
, and
Etzkorn F.A.
, J. Org. Chem. , 1997 , 62 , 8387 .
22.
Bauer U.
,
Egner B.J.
,
Nilsson I.
, and
Berghult M.
, Tetrahedron Lett. , 2001 , 41 , 2713 .
23.
Vounauwers K.
, and
Muller A.
, Ber. Dtsch. Chem. Ges. , 1908 , 41 , 4230 .
24.
Baker A.
, and
Butt V.S.
, J. Chem. Soc. , 1949 , 2142 .
25.
Khnor L.
, Ber. Dtsch. Chem. Ges. , 1893 , 26 , 100 .
26.
Garge H.G.
, and
Chandraprakash J.
, J. Pharm. Sci. , 1971 , 14 , 649 .
27.
Thakare V.G.
, and
Wadodkar K.N.
, Ind. Chem. Sect. , 1986 , 25 , 610 .
28.
ankhiwala M.D.
, and
Hathi M.V.
, J. Ind. Chem. Soc. , 1994 , 71 , 587 .
29.
Wang Y.
,
Vera C.I.R.
, and
Lin Q.
, Org. Lett. , 2007 , 9 , 4155 .
30.
Azarifar D.
, and
Maleki B.
, J. Heterocyclic Chem. , 2005 , 42 , 157 .
31.
Lee P.H.
,
Ahn H.
,
Lee K.
,
Sunga S.
, and
Kimb S.
, Tetrahedron Lett. , 2001 , 42 , 37 .
32.
Ryabukhin S.V.
,
Plaskon A.S.
,
Volochnyuk D.M.
,
Pipko S.E.
,
Shivanyuk A.N.
, and
Tolmachev A.A.
, J. Comb. Chem. , 2007 , 9 , 1073 .
33.
Yamanaka M.
,
Nishida A.
, and
Nakagawa M.
, J. Org. Chem. , 2003 , 68 , 3112 .
34.
Zhu Y.-l.
,
Huang S.-l.
, and
Pan Y.-j.
, Eur. J. Org. Chem. , 2005 , 2354 .
35.
Mayer S.
,
Daigle D.M.
,
Brown E.D.
,
Khatri J.
, and
Organ M.G.
, J. Comb. Chem. , 2004 , 6 , 776 .
36.
Yoshida Y.
,
Matsumoto N.
,
Hamasaki R.
, and
Tanabe Y.
, Tetrahedron Lett. , 1999 , 40 , 4227 .
37.
Robinson T.P.
,
Ehlers T.
,
Hubbard R.B.
IV
,
Bai X.
,
Arbiser J.L.
,
Goldsmith D.J.
, and
Bowen J.P.
, Bioorg. Med. Chem. Lett. , 2003 , 13 , 115 .
38.
Noya D.S.
, and
Pryor W.A.
, J. Am. Chem. Soc. , 1959 , 81 , 618 .
39.
Applequist D.E.
, and
Gdanski R.D.
, J. Org. Chem. , 1981 , 46 , 2502 .
40.
Palaska E.
,
Erol D.
, and
Demirdamar R.
Eur. J. Med. Chem. , 1996 , 31 , 43 .
41.
Chen Y.
,
Lam Y.
, and
Lai Y.-H.
, Org. Lett. , 2003 , 5 , 1067 .
