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Synthesis 2011(20): 3241-3246
DOI: 10.1055/s-0030-1260188
DOI: 10.1055/s-0030-1260188
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Novel Trinitrogen-Containing Triheterocycles via the Intramolecular Nitrile Oxide Cycloaddition Reaction
Further Information
Received
7 July 2011
Publication Date:
24 August 2011 (online)
Publication History
Publication Date:
24 August 2011 (online)
Abstract
The intramolecular nitrile oxide cycloaddition (INOC) reaction is applied to the synthesis of novel isoxazolooxazepinoindazole, benzoisoxazolodiazepinoindazolone, and spiro[isoxazoloazepine]piperidine heterocycles. Each of these targets incorporates a unique trinitrogen-containing triheterocyclic framework.
Keywords
alkenes - cycloadditions - heterocycles - pericyclic reactions - spiro compounds
- 1
Enev VS.Drescher M.Mulzer J. Tetrahedron 2007, 63: 5930 -
2a
Paek S.-M.Seo S.-Y.Kim S.-H.Jung J.-W.Lee Y.-S.Jung J.-K.Suh Y.-G. Org. Lett. 2005, 7: 3159 -
2b
Ghosh AK.Bilcer G.Schiltz G. Synthesis 2001, 2203 -
2c
List B.Castello C. Synlett 2001, 1687 - 3
Kim D.Lee J.Shim PJ.Lim JI.Doi T.Kim S.
J. Org. Chem. 2002, 67: 772 - 4
Duclos O.Dureault A.Depezay JC. Tetrahedron Lett. 1992, 33: 1059 -
5a
Nivlet A.Dechoux L.Le Gall T.Mioskowski C. Eur. J. Org. Chem. 1999, 3251 -
5b
Shing TKM.Zhong Y.-L. Synlett 2006, 1205 -
5c
Marrugo H.Dogbeavou R.Breau L. Tetrahedron Lett. 1999, 40: 8979 - 6
Shing TKM.Wong C.-H.Yip T. Tetrahedron: Asymmetry 1996, 7: 1323 - 7
Kozikowski AP.Mugrage BB.Wang BC.Xu Z. Tetrahedron Lett. 1983, 24: 3705 -
8a
Yeh M.-CP.Jou C.-F.Yeh W.-T.Chiu D.-Y.Reddy NRK. Tetrahedron 2005, 61: 493 -
8b
Arai N.Iwakoshi M.Tanabe K.Narasaka K. Bull. Chem. Soc. Jpn. 1999, 72: 2277 -
8c
Pal A.Bhattacharjee A.Bhattacharjya A.Patra A. Tetrahedron 1999, 55: 4123 - 9
Yip C.Handerson S.Jordan R.Tam W. Org. Lett. 1999, 1: 791 - 10
Jager V.Colinas PA. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, In The Chemistry of Heterocyclic Compounds Vol. 59:Padwa A.Pearson WH. John Wiley & Sons; New York: 2002. p.361-472 - 11
Kozikowski AP. Acc. Chem. Res. 1984, 17: 410 - 12
Müller V.Jäger V. Tetrahedron Lett. 1982, 23: 4777 - 13
Bode JW.Carreira EM. Org. Lett. 2001, 3: 1587 - 14
Aprison MH.Galvez-Ruano E.Lipkowitz KB.
J. Neurosci. Res. 1995, 41: 259 - 15
Arb VJ.Flores M.Muñoz P.Ruiz JR.Sánchez-Verdú P.Stud M. Liebigs Ann. 1995, 5: 817 - 16
Chambers MS.Baker R.Billington DC.Knight AK.Middlemiss DN.Wong EHF. J. Med. Chem. 1992, 11: 2033 - 17
Oakdale JS.Solano DM.Fettinger JC.Haddadin MJ.Kurth MJ. Org. Lett. 2009, 11: 2760 - 18
Avila B.Solano DM.Haddadin MJ.Kurth MJ. Org. Lett. 2011, 13: 1060 - 19
Sammelson RE.Miller RB.Kurth MJ. J. Org. Chem. 2000, 65: 2225 - 20
Houk KN.Sims J.Watts CR.Luskus LJ. J. Am. Chem. Soc. 1973, 95: 7301 -
21a
Donald MB.Conrad WE.Oakdale JS.Butler JD.Haddadin MJ.Kurth MJ. Org. Lett. 2010, 12: 2524 -
21b
Conrad WE.Fukazawa R.Haddadin MJ.Kurth MJ. Org. Lett. 2011, 13: 3138 -
22a
Butler JD.Solano DM.Robins LI.Haddadin MJ.Kurth MJ. J. Org. Chem. 2008, 73: 234 -
22b
Solano DM.Butler JD.Haddadin MJ.Kurth MJ. Org. Synth. 2010, 87: 339