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Synthesis 2001(12): 1818-1825
DOI: 10.1055/s-2001-17531
DOI: 10.1055/s-2001-17531
PAPER
© Georg Thieme Verlag Stuttgart · New York
N-Arylation of 1,4,7,10-Tetraazacyclododecanes
Weitere Informationen
Received
1 May 2001
Publikationsdatum:
11. August 2004 (online)
Publikationsverlauf
Publikationsdatum:
11. August 2004 (online)
Abstract
Palladium-catalyzed N-arylation reactions provide acces to N-aryl-substituted and N-aryl-bridged 1,4,7,10-tetraazacyclododecanes. Yields of arylation products are low with simple haloarenes, whereas reactions with pyridine derivatives give substituted cyclens in moderate to satisfactory yields.
Keywords
azamacrocycle - palladium - N-arylation
- 1
Kaden T.Weller H.Neuburger M.Zehnder M. Helv. Chim. Acta 1997, 80: 2315 - 2
Zhang XX.Izatt RM.Bradshaw JS.Krakowiak KE. Coord. Chem. Rev. 1998, 174: 179 - 3
Chantson TE.Hancock RD. Inorg. Chim. Acta 1995, 230: 165 - 4
Fabbrizzi L.Licchelli M.Pallavicini P.Perotti A.Taglietti A.Sacchi D. Chem.-Eur.J. 1996, 2: 75 - 5
Gaspar M.Grazina R.Bodor A.Farkas E.Santos MA. J. Chem. Soc., Dalton Trans. 1999, 799 - 6
Lecomte C.Dahaoui-Gindrey V.Chollet H.Gros C.Mishra AK.Barbette F.Pullumbi P.Guilard R. Inorg. Chem. 1997, 36: 3827 - 7
Luckay RC.Hancock RD. J. Chem. Soc., Dalton Trans. 1991, 1491 - 8
Kimura E.Kikuta E. Prog. React. Kinet. 2000, 25: 1 - 9
Fujioka H.Koike T.Yamada N.Kimura E. Heterocycles 1996, 42: 775 - 10
Koike T.Takashige M.Kimura E.Fujioka H.Shiro M. Chem.-Eur. J. 1996, 2: 617 - 11
Aoki S.Kimura E. J. Am. Chem. Soc. 2000, 122: 4542 - 12
Kimura E.Koike T. Chem. Commun. 1998, 1495 - 13
König B.Pelka M.Klein M.Dix I.Jones PG.Lex J. J. Inclusion Phenom. 2000. 37: p.39 , and cited references - 14
Denat F.Brandes S.Guilard R. Synlett 2000, 561 - 15
Filali A.Yaouanc J.-J.Handel H. Angew. Chem. Int. Ed. Engl. 1991, 30: 560 - 16
Hartwig JF. Acc. Chem. Res. 1998, 31: 852 - 17
Singer RA.Sadighi JP.Buchwald SL. J. Am. Chem. Soc. 1998, 120: 213 - 18
Brandes S.Gros C.Denat F.Pullumbi P.Guilard R. Bull. Soc. Chim. Fr. 1996, 133: 65 - 19
Koike T.Gotoh T.Aoki S.Kimura E.Shiro M. Inorg. Chim. Acta 1998, 270: 424 - 20
Wolfe JP.Buchwald SL. J. Org. Chem. 2000, 65: 1144 - 21
Wolfe JP.Sadighi HT.Yin J.Buchwald SL. J. Org. Chem. 2000, 65: 1158 - 22
Wolfe JP.Marcoux J.-F.Buchwald SL. Acc. Chem. Res. 1998, 31: 805 - 23
Old DW.Harris MC.Buchwald SL. Org. Lett. 2000, 2: 1403 - 24
Mann G.Hartwig JF.Driver MS.Fernández-Rivas C. J. Am. Chem. Soc. 1998, 120: 827 - 25
Lam PYS.Deudon S.Averill KM.Li R.He MY.DeShong P.Clark CG. J. Am. Chem. Soc. 2000, 122: 7600 - 26
Zhang X.-X.Buchwald SL. J. Org. Chem. 2000, 65: 8027 - 27
Witulski B. Synlett 1999, 1223 - 28
Wolfe JP.Buchwald SL. J. Org. Chem. 1997, 62: 6066 - 30
Wolfe JP.Buchwald SL. Angew. Chem. Int. Ed. 1999, 38: 2413 - 31
Zhang X.-X.Buchwald SL. J. Org. Chem. 2000, 65: 8027 - 32
Tamaru Y.Yamada Y.Yoshida Z. Synthesis 1983, 474 - 33
Hatanaka Y.Goda K.Okahara Y. Tetrahedron 1994, 50: 8301 - 34
Hirano T.Kikuchi K.Urano Y.Higuchi T.Nagano T. Angew. Chem. Int. Ed. 2000, 39: 1052 - 35
Prasad JS.Okuniewicz FJ.Delaney EJ.Dischino DD. J. Chem. Soc., Perkin Trans. 1 1991, 3329 - 36
Dumont A.Jacques V.Qixiu P.Desreux JF. Tetrahedron Lett. 1994, 35: 3707
References
The calculation was performed with the modelling software SPARTAN using the MMFF force field and a conformer search algorithm.