Abstract
A stepwise preparation of a series of nitrogen-containing 25-membered pentaolefinic macrocycles is presented. The corresponding arenesulfonamides and trans -1,4-dibromo-2-butene served as precursors for the synthesis.
Key words
alkenes - heterocycles - macrocycles - sulfonamides
References
1 Dietrich B.
Viout P.
Lehn J.-M.
Aspects de la Chimie des Composés Macrocycliques
InterEditions/Editions de CNRS;
Paris:
1991.
2 Takemura H.
Shinmyozu T.
Inazu T.
Coord. Chem. Rev.
1996,
156:
183
3 Cerezo S.
Cortés J.
López-Romero J.-M.
Moreno-Mañas M.
Parella T.
Pleixats R.
Roglans A.
Tetrahedron
1998,
54:
14885
4 Cerezo S.
Cortés J.
Galvan D.
López-Romero J.-M.
Moreno-Mañas M.
Pleixats R.
Avilés F.-X.
Canals F.
Roglans A.
Rapid Commun. Mass Spectrom.
1999,
13:
2359
5 Munekata E.
Ishiyama H.
Osakada F.
Izumi K.
Peptide Chem.
1980,
18:
181
6a Moreno-Mañas M.
Pleixats R.
Roglans A.
Sebastián RM.
Vallribera A.
Arkivoc
2004,
Part IV:
109 ; (http://www.arkat-usa.org)
6b Moreno-Mañas M.
Pleixats R.
Sebastián RM.
Vallribera A.
Roglans A.
J. Organomet. Chem.
2004,
689:
3669
7a Ogoshi S.
Morita M.
Inoue K.
Kurosawa H.
J. Organomet. Chem.
2004,
689:
662
7b Taube R.
Wache S.
Sieler J.
Kempe R.
J. Organomet. Chem.
1993,
456:
131
7c Taube R.
Wache S.
Sieler J.
J. Organomet. Chem.
1993,
459:
335
7d Pörschke R.
Kleimann W.
Tsay Y.-H.
Krüger C.
Wilke G.
Chem. Ber.
1990,
123:
1267
7e Wilke G.
Angew. Chem., Int. Ed. Engl.
1988,
27:
185
7f Ferrara JD.
Tanaka AA.
Fierro C.
Tessier-Youngs CA.
Youngs WJ.
Organometallics
1989,
8:
2089
7g Lewandos GS.
Gregston DK.
Nelson FR.
J. Organomet. Chem.
1976,
118:
363
7h Faure R.
Loiseleur H.
Haufe G.
Trauer H.
Acta Crystallogr. Sect. C
1985,
41:
1593
7i Jackson RB.
Streib WE.
J. Am. Chem. Soc.
1967,
89:
2539
7j Iyoda M.
Kuwatani Y.
Yamauchi T.
Oda M.
J. Chem. Soc., Chem. Commun.
1988,
65
7k Yoshida T.
Kuwatani Y.
Hara K.
Yoshida M.
Matsuyama H.
Iyoda M.
Nagase S.
Tetrahedron Lett.
2001,
42:
53
7l Kuwatani Y.
Yoshida T.
Kusaka A.
Oda M.
Hara K.
Yoshida M.
Matsuyama H.
Iyoda M.
Tetrahedron
2001,
57:
3567
7m Chow YL.
Cheng XE.
Buono-Core GE.
Organometallics
1987,
6:
1126
7n Salomon RG.
Kochi JK.
J. Organomet. Chem.
1974,
64:
135
7o Salomon RG.
Kochi JK.
J. Am. Chem. Soc.
1973,
95:
1889 ; and also ref.7j-l
8 Crystallographic data (excluding structure factors) for the structure in this paper has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 230218. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
9 Neustadt BR.
Tetrahedron Lett.
1994,
35:
379
10 Cortés J.
Moreno-Mañas M.
Pleixats R.
Eur. J. Org. Chem.
2000,
239
11 Cerezo S.
Cortés J.
Galvan D.
Lago E.
Marchi C.
Molins E.
Moreno-Mañas M.
Pleixats R.
Torrejón J.
Vallribera A.
Eur. J. Org. Chem.
2001,
329
12 Moreno-Mañas M.
Spengler J.
Tetrahedron
2002,
58:
7769
13a Badetti E.
Master in Chemical Experimentation
Universitat Autònoma de Barcelona;
Barcelona Spain:
2003.
13b It gave correct elemental analysis.
14 Slocum DW.
Achermann W.
Synth. React. Inorg. Met. Org. Chem.
1982,
12:
397
15 Llobet A.
Masllorens E.
Moreno-Mañas M.
Pla-Quintana A.
Rodríguez M.
Roglans A.
Tetrahedron Lett.
2002,
43:
1425
16 Llobet A.
Masllorens E.
Rodríguez M.
Roglans A.
Benet-Buchholz J.
Eur. J. Inorg. Chem.
2004,
1601
17 Hajduk PJ.
Shuker SB.
Nettesheim DG.
Craig R.
Augeri DJ.
Betebenner D.
Albert DH.
Guo Y.
Meadows RP.
Xu L.
Michaelides M.
Davidsen SK.
Fesik SW.
J. Med. Chem.
2002,
45:
5628
