Abstract
An efficient parallel synthesis of a representative 28-member library of phthalimides
is described. Parallel chromatography afforded the library members in suitable purity
and with high yields.
Key words
library - microwave - phthalimide - 2-aryl-1H -isoindole-1,3-dione - TNF-α
References
For some recent biological applications, see:
<A NAME="RG31501ST-1A">1a </A>
Shimazawa R.
Miyachi H.
Takayama H.
Kuroda K.
Kato F.
Kato M.
Hashimoto Y.
Biol. Pharm. Bull.
1999,
22:
224
<A NAME="RG31501ST-1B">1b </A>
Da Settimo A.
Primofiore G.
Da Settimo F.
Simorini F.
La Motta C.
Martinelli A.
Boldrine E.
Eur. J. Med. Chem.
1996,
31:
49
<A NAME="RG31501ST-1C">1c </A>
Shibata Y.
Sasaki K.
Hashimoto Y.
Iwasaki S.
Chem. Pharm. Bull.
1996,
44:
156
<A NAME="RG31501ST-1D">1d </A>
Langmuir ME.
Yang J.-R.
Moussa AM.
Laura R.
Lecompte KA.
Tetrahedron Lett.
1995,
36:
3989
<A NAME="RG31501ST-1E">1e </A>
Mayer A.
Neuenhofer S.
Angew. Chem. Int. Ed. Engl.
1994,
33:
1044
<A NAME="RG31501ST-1F">1f </A>
Rusiecki VK.
Warner SA.
Bioorg. Med. Chem. Lett.
1993,
3:
707
<A NAME="RG31501ST-2A">2a </A>
Reddy PY.
Kondo S.
Toru T.
Ueno Y.
J. Org. Chem.
1997,
62:
2652 ; and references cited therein
<A NAME="RG31501ST-2B">2b </A>
Ohkubo M.
Nishimura T.
Jona H.
Honma T.
Morishima H.
Tetrahedron
1996,
52:
8099
<A NAME="RG31501ST-3">3 </A>
Iijima T.
Suzuki N.
Fukuda W.
Tomoi M.
J. Eur. Polym.
1995,
31:
775
<A NAME="RG31501ST-4A">4a </A>
Walker MA.
J. Org. Chem.
1995,
60:
5352
<A NAME="RG31501ST-4B">4b </A>
Walker MA.
Tetrahedron Lett.
1994,
35:
665
<A NAME="RG31501ST-5">5 </A>
Bogdal D.
Pielichowsky J.
Boron A.
Synlett
1996,
873
For recent papers see:
<A NAME="RG31501ST-6A">6a </A>
Vidal T.
Petit A.
Loupy A.
Gedye RN.
Tetrahedron
2000,
56:
5473
<A NAME="RG31501ST-6B">6b </A>
Seijas JA.
Vazquez-Tato P.
Martinez MM.
Nuñez-Corredoira G.
J. Chem. Res. (S)
1999,
420
<A NAME="RG31501ST-6C">6c </A>
Varma RS.
Dahiya R.
Kumar S.
Tetrahedron Lett.
1997,
38:
2039
<A NAME="RG31501ST-7A">7a </A>
Chandrasekhar S.
Padmaja NB.
Raza A.
Synlett
1999,
1597
<A NAME="RG31501ST-7B">7b </A>
Chandrasekhar S.
Takhi M.
Uma G.
Tetrahedron Lett.
1997,
38:
8089
<A NAME="RG31501ST-8">8 </A>
Borah NH.
Boruah RC.
Sandhus JS.
J. Chem. Res.(S)
1998,
272
Parallel synthesis in microwave ovens has been described to prepare thioamide and
pyridine libraries:
<A NAME="RG31501ST-9A">9a </A>
Olsson R.
Hansen HC.
Andersson C.-M.
Tetrahedron Lett.
2000,
41:
7947
<A NAME="RG31501ST-9B">9b </A>
Cotterill IC.
Usyatinsky AY.
Arnold JM.
Clark DS.
Dordick JS.
Michels PC.
Khmelnitsky YL.
Tetrahedron Lett.
1998,
39:
1117
<A NAME="RG31501ST-10">10 </A> Microwave irradiation was carried out with a Sanyo microwave oven (EM-S100, 800,
with a maximum power output of 800 W) calibrated by a standard procedure:
Watkins KW.
J. Chem. Ed.
1983,
60:
1043
<A NAME="RG31501ST-11">11 </A>
Acquired from International Sorbent Technology Ltd., U.K.
<A NAME="RG31501ST-12">12 </A>
Savant Automatic Environmental SpeedVac (AES 2000) was used.
<A NAME="RG31501ST-13">13 </A>
Microsoft® Excel 97 was used.
<A NAME="RG31501ST-14">14 </A>
Shibata Y.
Sasaki K.
Hashimoto Y.
Iwasaki S.
Chem. Pharm. Bull.
1996,
44:
156
<A NAME="RG31501ST-15">15 </A>
Kamal A.
Laxman E.
Laxman N.
Rao V.
Tetrahedron Lett.
1998,
39:
8733
<A NAME="RG31501ST-16">16 </A>
Pagani G.
Baruffini A.
Borgna P.
Caccialanza G.
Farmaco, Ed. Sci.
1968,
23:
448 ; Chem. Abstr . 1969 , 69 , 43588
<A NAME="RG31501ST-17">17 </A>
Miyachi H.
Azuma A.
Ogasawara A.
Uchimura E.
Watanabe N.
Kobayashi Y.
Kato F.
Kato M.
Hashimoto Y.
J. Med. Chem.
1997,
40:
2858
<A NAME="RG31501ST-18">18 </A> Fifolt M. J., Sojka S. A., Wolfe R. A., Hojnicki D. S., Bieron J. F., Dinan F.
J.; J. Org. Chem.; 1989 , 54 : 3019
<A NAME="RG31501ST-19">19 </A>
Abdel-Rahman AE.
Khalil ZH.
Bull. Chem. Soc. Jpn.
1978,
51:
2148
<A NAME="RG31501ST-20">20 </A>
Krische MJ.
Lehn JM.
Kyritsakas N.
Fisher J.
Helv. Chim. Acta
1998,
81:
1909
<A NAME="RG31501ST-21">21 </A>
Perry RJ.
Turner R.
J. Org. Chem.
1991,
56:
6573
<A NAME="RG31501ST-22">22 </A>
Hokko Chemical Industry Co. Ltd., Jpn. Kokai Tokkyo Koh, 1980 , Jp55136210A2; Chem. Abstr. 1980 , 94 , 78435.
<A NAME="RG31501ST-23">23 </A>
Hasimoto Y. inventors; PCT Int. Appl. WO9807421.
; Chem. Abstr. 1998, 128 , 204894.