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Synthesis 2005(13): 2210-2214
DOI: 10.1055/s-2005-869968
DOI: 10.1055/s-2005-869968
PAPER
© Georg Thieme Verlag Stuttgart · New York
A Versatile Approach to the Synthesis of Pendant Benzodiazacoronands
Further Information
Received
16 February 2005
Publication Date:
24 June 2005 (online)
Publication History
Publication Date:
24 June 2005 (online)

Abstract
A versatile approach to the synthesis of pendant benzodiazacoronands is presented. Macrocyclic compounds possessing intra-annular amine or hydroxy group were obtained and N-benzamide, O-benzyl or O-benzoyl side-arms were introduced into such a macrocyclic framework. Mild conditions and satisfactory yield of presented synthetic pathways offer a wide and easy access to new macrocyclic compounds having different pendant arms.
Key words
amides - diazo compounds - macrocycles - receptors - supramolecular chemistry
-
1a
Reinhoudt DN.Hall RH.van der Leij M.Oosterink HJ. Tetrahedron 1981, 37: 3661 -
1b
Richards PT.Hamilton AD. J. Chem. Soc., Chem. Commun. 1985, 1198 -
1c
Czech A.Czech BP.Bartsch RA. J. Org. Chem. 1988, 53: 5 -
1d
Skowrońska-Ptasińska M.Aarts VM.Egberink RJ.van Eerden J.Harkema S.Reinhoudt DN. J. Org. Chem. 1988, 53: 5484 -
1e
Kenda T.Misumi S.Ishizaki Y.Kai Y.Kasai N.Hirao G. J. Am. Chem. Soc. 1988, 110: 2970 -
1f
Chapoteau E.Czech BP.Kumar A.Pose A.Bartsch RA.Holwerda RA.Dalley NK.Wilson BE.Weining J. J. Org. Chem. 1989, 54: 86 - 2
Piątek P.Gryko DT.Szumna A.Jurczak J. Tetrahedron 2004, 60: 5769 - 3
Shinkai S.Miyazaki K.Manabe O. J. Chem. Soc., Perkin Trans. 1 1987, 449 - 4
Piątek P.Jurczak J. Chem. Commun. 2002, 2450 - For selected reviews, see:
-
5a
Vögtle F.Neumann P. Top. Curr. Chem. 1974, 48: 67 -
5b
Vögtle F.Hohner G. Top. Curr. Chem. 1978, 74: 1 -
5c
Boekelheide V. Acc. Chem. Res. 1980, 13: 65 -
5d
Chan T.-H.Kang GJ. J. Org. Chem. 1985, 50: 452 -
5e
Collet A.Dutasta J.-P.Lozach B.Canceill J. Top. Curr. Chem. 1993, 165: 103 -
5f
Hochmuth DH.König WA. Liebigs Ann. 1996, 947 -
6a
Kalisiak J.Jurczak J. Synlett 2004, 1616 -
6b
Piątek P.Kalisiak J.Jurczak J. Tetrahedron Lett. 2004, 45: 3309 -
7a
Dietrich B.Lehn J.-M.Sauvage JP. Tetrahedron 1973, 29: 1629 -
7b
Krakowiak KE.Bradshaw JS.Zamecka-Krakowiak DJ. Chem. Rev. 1989, 89: 929 -
7c
Bradshaw JS.Krakowiak KE.Izatt RM. Aza Crown Macrocycles John Wiley & Sons; New York: 1993. -
8a
Gryko DT.Piątek P.Pêcak A.Pays M.Jurczak J. Tetrahedron 1998, 54: 7505 -
8b
Gryko DT.Gryko D.Jurczak J. Synlett 1999, 1310 - 9
Gryko DT.Piątek P.Jurczak J. Synthesis 1999, 336 -
10a
Bakó P.Fenichel L.Tőke L. Liebigs Ann. Chem. 1990, 1161 -
10b
Pigot T.Duriaez M.-C.Cazaux L.Picard C.Tisnes T. J. Chem. Soc., Perkin Trans. 2 1993, 221 -
10c
Solov’ev VP.Strakhova NN.Kazachenko VP.Solotnov AF.Baulin VE.Raevsky OA.Rudiger V.Eblinger F.Schneider H.-J. Eur. J. Org. Chem. 1998, 1379 -
10d
Gryko DT.Pêcak A.Koźmiński W.Piątek P.Jurczak J. Supramol. Chem. 2000, 12: 229 -
11a
Huszthy P.Bradshaw JS.Zhu YC.Wang T.Dalley NK.Curtis JC.Izatt RM. J. Org. Chem. 1992, 57: 5383 -
11b
Nazarenko AY.Huszthy P.Bradshaw JS.Lamb JD.Izatt RM. J. Incl. Phenom. 1995, 20: 13 -
12a
Chang SK.Hamilton AD. J. Am. Chem. Soc. 1988, 110: 1318 -
12b
Tellado FG.Goswami S.Chang SK.Geib SJ.Hamilton AD. J. Am. Chem. Soc. 1990, 112: 7393 -
13a
Schmidtchen FP.Berger M. Chem. Rev. 1997, 97: 1609 -
13b
Kubik S.Goddard R. J. Org. Chem. 1999, 64: 9475 -
13c
Bondy CR.Loeb SJ. Coord. Chem. Rev. 2003, 240: 77 -
13d
Choi K.Hamilton AD. Coord. Chem. Rev. 2003, 240: 101 - 14
Stetter H.Hoehe K. Chem. Ber. 1958, 91: 1123 - 15
Yu MJ.McCowan JR.Phebus LA.Towner RD.Ho PPK.Keith PT.Luttman CA.Saunders RD.Ruterbories KJ.Lindstrom TD.Wikel JH.Morgan E.Hahn RA. J. Med. Chem. 1993, 36: 1262 - 16
Gryko DT.Piątek P.Jurczak J. Tetrahedron 1997, 53: 795