Subscribe to RSS
DOI: 10.1055/s-0028-1083537
Novel Extensions of the tert-Amino Effect: Formation of Phenanthridines and Diarene-Fused Azocines from ortho-ortho′-Functionalized Biaryls
Publication History
Publication Date:
15 October 2008 (online)

Abstract
Phenanthridines and azocines fused to two benzene rings or one benzene and one pyridazinone ring, which are otherwise difficult to access, were prepared via two new extensions of the tert-amino effect. The synthetic pathway includes three steps: i) Suzuki reaction of an ortho-functionalized phenylboronic acid with ortho-disubstituted benzenes or pyridazinones; ii) the Knoevenagel condensation reaction of the biaryl aldehydes formed with active methylene compounds to obtain vinyl derivatives or, through their cyclization, phenanthridines via a tert-amino effect; and iii) thermal isomerization of vinyl or phenanthridinium compounds to fused azocines via another type of tert-amino effect.
Key words
tert-amino effect - dibenzazocines - pyridazinobenzazocines - nonbonding interactions - Suzuki reaction
- Supporting Information for this article is available online:
- Supporting Information (PDF)
- 1
Meth-Cohn O.Suschitzky H. Adv. Heterocycl. Chem. 1972, 14: 211 - 2a
Meth-Cohn O. Adv. Heterocycl. Chem. 1996, 65: 1Reference Ris Wihthout Link - 2b
Quintela JM. Rec. Res. Dev. Org. Chem. 2003, 7: 259Reference Ris Wihthout Link - 3a
Nijhuis WHN.Verboom W.Reinhoudt DN. J. Am. Chem. Soc. 1987, 109: 3136Reference Ris Wihthout Link - 3b
Groenen LC.Verboom W.Nijhuis WHN.Reinhoudt DN.van Hummel GJ.Feil D. Tetrahedron 1988, 44: 4637Reference Ris Wihthout Link - 3c
Nijhuis WHN.Verboom W.Abu El-Fadl A.Harkema S.Reinhoudt DN. J. Org. Chem. 1989, 54: 199Reference Ris Wihthout Link - 3d
Nijhuis WHN.Verboom W.Abu El-Fadl A.van Hummel GJ.Reinhoudt DN. J. Org. Chem. 1989, 54: 209Reference Ris Wihthout Link - 3e
Ojea V.Muinelo I.Figueroa MC.Ruiz M.Quintela JM. Synlett 1995, 622Reference Ris Wihthout Link - 3f
D’yachenko EV.Glukhareva TV.Dyudya LV.Eltsov OV.Morzherin YY. Molecules 2005, 10: 1101Reference Ris Wihthout Link - 3g
Tverdokhlebov AV.Gorulya AP.Tolmachev AA.Kostyuk AN.Chernega AN.Rusanov EB. Tetrahedron 2006, 62: 9146Reference Ris Wihthout Link - 4a
Mátyus P.Fuji K.Tanaka K. Heterocycles 1994, 37: 171Reference Ris Wihthout Link - 4b
Schwartz A.Beke G.Kovári Z.Böcskey Z.Farkas .Mátyus P. J. Mol. Struct. 2000, 528: 49Reference Ris Wihthout Link - 4c
Károlyházi L.Regdon G.Éliás O.Beke G.Tábi T.Hódi K.Erõs I.Mátyus P. J. Mol. Struct. 2003, 666-667: 667Reference Ris Wihthout Link - 4d
Kaval N.Dehaen W.Mátyus P.Van der Eycken E. Green Chem. 2004, 6: 125Reference Ris Wihthout Link - 4e
Kaval N.Halász-Dajka B.Vo-Thanh G.Dehaen W.Van der Eycken J.Mátyus P.Loupy A.Van der Eycken E. Tetrahedron 2005, 61: 9052Reference Ris Wihthout Link - 4f
Mátyus P.Éliás O.Tapolcsányi P.Polonka-Bálint .Halász-Dajka B. Synthesis 2006, 2625Reference Ris Wihthout Link - 4g
Dajka-Halász B.Földi A.Ludányi K.Mátyus P. Arkivoc 2008, (iii): 102Reference Ris Wihthout Link - 5a
Meth-Cohn O.Taylor DL. J. Chem. Soc., Chem. Commun. 1995, 14: 1463Reference Ris Wihthout Link - 5b
Cheng Y.Meth-Cohn O.Taylor D. J. Chem. Soc., Perkin Trans. 1 1998, 7: 1257Reference Ris Wihthout Link - 6a
Brossi A.Boyé O.Muzaffar A.Yeh HJC.Toome V.Wegrzynski B.George C. FEBS Lett. 1990, 262: 5Reference Ris Wihthout Link - 6b
Brossi A. J. Med. Chem. 1990, 33: 2311Reference Ris Wihthout Link - 6c
Berg U.Bladh H.Svensson C.Wallin M. Bioorg. Med. Chem. Lett. 1997, 7: 2771Reference Ris Wihthout Link - 6d
Brecht R.Seitz G.Guénard D.Thoret S. Bioorg. Med. Chem. 2000, 8: 557Reference Ris Wihthout Link - 6e
Bergemann S.Brecht R.Büttner F.Guénard D.Gust R.Seitz G.Stubbs MT.Thoret S. Bioorg. Med. Chem. 2003, 11: 1269Reference Ris Wihthout Link - 7
Lauer M.Wulff G. J. Organomet. Chem. 1983, 256: 1 - 8
Verboom W.Reinhoudt DN.Visser R.Harkema S. J. Org. Chem. 1984, 49: 269 - 9
Konecny V.Kovac S.Varkonda S. Collect. Czech. Chem. Commun. 1985, 50: 492 - 10
O’Leary J.Wallis JD.Wood ML. Acta Crystallogr., Sect. C 2001, 57: 851 - 11a
Maes BUW.R’kyek O.Košmrlj J.Lemière GLF.Esmans E.Rozenski J.Dommisse RA.Haemers A. Tetrahedron 2001, 57: 1323Reference Ris Wihthout Link - 11b
Riedl Z.Maes BUW.Monsieurs K.Lemière GLF.Mátyus P.Hajós G. Tetrahedron 2002, 58: 5645Reference Ris Wihthout Link - 11c
Tapolcsányi P.Maes BUW.Monsieurs K.Lemière GLF.Riedl Z.Hajós G.Van den Driessche B.Dommisse RA.Mátyus P. Tetrahedron 2003, 59: 5919Reference Ris Wihthout Link - 11d
Riedl Z.Monsieurs K.Krajsovszky G.Dunkel P.Maes BUW.Tapolcsányi P.Egyed O.Boros S.Mátyus P.Pieters L.Lemière GLF.Hajós G. Tetrahedron 2006, 62: 121Reference Ris Wihthout Link - 13a
O’Leary J.Bell PC.Wallis JD.Schweizer WB. J. Chem. Soc., Perkin Trans. 2 2001, 133Reference Ris Wihthout Link - 13b
O’Leary J.Formosa X.Skranc W.Wallis JD. Org. Biomol. Chem. 2005, 3: 3273Reference Ris Wihthout Link
References and Notes
The X-ray data are available from the Cambridge Crystallographic Data Centre CCDC under the numbers 692718-692722 for 7b, 13a, 16c, 19a, and 23a, respectively. 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. The details of the X-ray structures will be published elsewhere.
14Dunkel, P.; Földi, Á. A.; Mátyus, P. unpublished results.
15The experimental details are available in the Supporting Information.