RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2008(13): 2141-2147
DOI: 10.1055/s-2008-1067125
DOI: 10.1055/s-2008-1067125
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Concise Synthesis of Mono- and Polysubstituted and Diversely N-Functionalized Isoindolinones and Isoquinolones
Weitere Informationen
Received
4 April 2008
Publikationsdatum:
11. Juni 2008 (online)
Publikationsverlauf
Publikationsdatum:
11. Juni 2008 (online)

Abstract
A variety of differently substituted and diversely N-(sulfanyl)hydroxyalkyl functionalized isoindolinones and isoquinolones have been obtained by anionic cyclization of cyclic bromobenzyl or bromophenethylcarbamates and thiocarbamates.
Key words
lactams - carbanions - ring closure - ring opening - bicyclic compounds
-
1a
Fajardo V.Elango V.Cassels BK.Shamma M. Tetrahedron Lett. 1982, 23: 39 -
1b
Pendrak I.Barney S.Wittrock R.Lambert DM.Kingsbury WD. J. Org. Chem. 1994, 59: 2623 -
1c
De Clercq E. J. Med. Chem. 1995, 38: 2491 -
1d
Bellioti TR, andWustrow DJ. inventors; US Patent 6087364. ; Chem. Abstr. 2000, 133, 89548 -
1e
Hudkins RL,Reddy D,Singh J,Stripathy R, andUnderiner TL. inventors; PCT Int. Appl. WO 0047583. ; Chem. Abstr. 2000, 133, 177158 -
1f
Duggan ME,Hartman GD, andHoffman WF. inventors; PCT Int. Appl. WO 9737655. ; Chem. Abstr. 1997, 127, 331749 - 2
Govindachari TR.Ravindranath KR.Viswanathan N. J. Chem. Soc., Perkin Trans. 1 1974, 1215 -
3a
Taylor EC.Zhou P.Jenning LD.Mao Z.Hu B.Jun J.-G. Tetrahedron Lett. 1997, 38: 521 -
3b
Fuska J.Fuskova A.Proksa B. Zb. Pr. Chemickotechnol. Fak., SVST, 1979-1981 (pub. 1986), 285-291 ; Chem. Abstr. 1987, 106, 95582 - 4
Li S.Wang X.Guo H.Chen L. Yiyano Gongye 1985, 16: 543 ; Chem. Abstr. 1986, 105, 6378 -
5a
Linden M.Hadler D.Hofmann S. Hum. Psychopharmacol. 1997, 12: 445 -
5b
Norman MH.Minick DJ.Rigdon GC. J. Med. Chem. 1996, 39: 149 - 6
Lippmann W. inventors; US Patent 4267189. ; Chem. Abstr. 1981, 95, 61988 - 7
Yeo H.Li Y.Fu L.Zhu J.-L.Gullen EA.Dutschman GE.Lee Y.Chung R.Huang E.-S.Austin DJ.Cheng Y.-C. J. Med. Chem. 2005, 48: 534 - 8
Zeldis JB. inventors; PCT Int. Appl. WO 043378. ; Chem. Abstr. 2004, 140, 417925 - 9
Ren J.Esnouf RM.Hopkins AL.Stuart DI.Stammers DK. J. Med. Chem. 1999, 42: 3845 - 10
Zhuang Z.-P.Kung M.-P.Mu M.Kung HF. J. Med. Chem. 1998, 41: 157 -
11a
Parham WE.Bradsher CK. Acc. Chem. Res. 1982, 15: 300 -
11b
Wakefield BJ. The Chemistry of Organolithium Compounds Pergamon; New York: 1990. 2nd ed. -
11c
Gray M.Tinkl M.Snieckus V. In Comprehensive Organometallic Chemistry II Vol. 11:Abel EW.Stone FGA.Wilkinson G. Pergamon; Oxford: 1995. p.66-92 -
11d
Ardeo A.Collado MI.Osante I.Ruiz J.Sotomayor N.Lete E. In Targets in Heterocyclic Systems Vol. 5:Atanassi O.Spinelli D. Italian Society of Chemistry; Rome: 2001. p.393-418 -
11e
Clayden J. Organolithiums: Selectivity for Synthesis Elsevier; Oxford: 2002. -
11f
Sotomayor N.Lete E. Curr. Org. Chem. 2003, 7: 275 - 12
Lipshutz BH.Liu Z.-P.Kayser F. Tetrahedron Lett. 1994, 35: 5567 - 13
Paleo MR.Castedo L.Dominguez D. J. Org. Chem. 1993, 58: 2763 - 14
Markus A. Synthesis 1996, 230 - 15
Dai-Ho G.Mariano PS. J. Org. Chem. 1987, 52: 704 - 16
Al-Maharik N.Engman L.Malmstroem J.Schiesser CH. J. Org. Chem. 2001, 66: 6286 - 17
Wilmore BH.Cassidy PB.Warters RL.Roberts JC. J. Med. Chem. 2001, 44: 2661 - 18
Kim YJ.Varma RS. Tetrahedron Lett. 2004, 45: 7205 - 19
Schneider M. Chem. Ber. 1960, 93: 1579