Abstract
para -Substituted N -phenylpyrrolidines, -piperidines, -perhydroazepines and -morpholines react with
oxalyl chloride and DABCO to give the pharmaceutically useful intermediates, N -ω-haloalkylisatins, under mild conditions and generally good yields.
Key words
cyclic t -anilines - oxalyl chloride - DABCO -
N -ω-haloalkylisatins
References
<A NAME="RE06001SS-1">1 </A>
Teraji T,
Oku T, and
Namiki T. inventors; Eur. Patent 10398.
; Chem. Abstr. 1980 , 93 , 220773
<A NAME="RE06001SS-2">2 </A>
Kobayashi M, and
Kitazawa MY. inventors; Japanese Patent 62270576.
; Chem. Abstr. 1988 , 109 , 110263
<A NAME="RE06001SS-3">3 </A>
Boar BR, and
Cross AJ. inventors; WO Patent 9312085.
; Chem. Abstr. 1993 , 119 , 225964
<A NAME="RE06001SS-4">4 </A>
Boar BR,
O’shea DM, and
Tomlinson ID. inventors; WO Patent 9429272.
; Chem. Abstr. 1995 , 122 , 239179
<A NAME="RE06001SS-5">5 </A>
Gallagher PT,
Owton WM, and
Smith CW. inventors; Eur. Patent 780388.
; Chem. Abstr. 1997 , 127 , 135719
<A NAME="RE06001SS-6">6 </A>
Rekhter MA.
Radul OM.
Bukhanyuk SM.
Chem. Heterocycl. Compd. (Engl. Trans.)
1999,
35:
792
<A NAME="RE06001SS-7">7 </A>
Cheng Y.
Ye HL.
Zhan YH.
Meth-Cohn O.
Synthesis
2001,
904
<A NAME="RE06001SS-8">8 </A>
Venuti MC.
Ort O.
Synthesis
1988,
985
<A NAME="RE06001SS-9">9 </A>
Juaristi E.
Madrigal D.
Tetrahedron
1989,
45:
629
<A NAME="RE06001SS-10">10 </A>
Sellers C.
Suschitzky H.
J. Chem. Soc.
1965,
6186
<A NAME="RE06001SS-11">11 </A>
Shim SC.
Huh KT.
Park WH.
Tetrahedron
1986,
42:
259
<A NAME="RE06001SS-12">12 </A>
Beach SF.
Hepworth JD.
Sawyer J.
Hallas G.
Marsden R.
Mitchell MM.
Ibbitson DA.
Jones AM.
Neal GT.
J. Chem. Soc., Perkin 2
1984,
217
<A NAME="RE06001SS-13">13 </A>
Barton DHR.
Donnelly DMX.
Finet J.-P.
Guiry PJ.
J. Chem. Soc., Perkin Trans. 1
1991,
2095
<A NAME="RE06001SS-14">14 </A>
Fielden R.
Meth-Cohn O.
Suschitzky H.
J. Chem. Soc., Perkin Trans. 1
1973,
696
<A NAME="RE06001SS-15">15 </A>
Shim SC.
Doh CH.
Kim TJ.
Lee HK.
Kim KD.
J. Heterocycl. Chem.
1988,
25:
1383
<A NAME="RE06001SS-16">16 </A>
Stauffer SR.
Lee S.
Stambuli JP.
Hauek SI.
Hartwig JF.
Org. Lett.
2000,
2:
1423
<A NAME="RE06001SS-17">17 </A>
Birch AJ.
Hutchinson EG.
Rao GS.
J. Chem. Soc. (C)
1971,
637
<A NAME="RE06001SS-18">18 </A>
Pearson AJ.
Gelormini AM.
J. Org. Chem.
1994,
59:
4561
<A NAME="RE06001SS-19">19 </A>
Jones DH.
J. Chem. Soc.(C)
1971,
132