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Synthesis 2011(4): 669-673
DOI: 10.1055/s-0030-1258416
DOI: 10.1055/s-0030-1258416
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkRing-Closing Metathesis Approach to 2H-2-Benzazepine-1,3-diones
Further Information
Received
1 December 2010
Publication Date:
19 January 2011 (online)
Publication History
Publication Date:
19 January 2011 (online)

Abstract
A series of diversely substituted 2H-2-benzazepine-1,3-diones were efficiently prepared from the unsaturated precursors, N-acyl-o-vinylbenzamides, through a ring-closing metathesis reaction. The parent compounds were easily obtained from the appropriate o-vinylbenzoic acids.
Key words
fused-ring systems - acylation - ring closure - metathesis - imides
- 1
Horton DA.Bourne GT.Smythe ML. Chem. Rev. 2003, 103: 893 - 2a
Miller WH.Alberts DP.Bhatnagar PK.Bondinell WE.Callahan JF.Calvo RR.Cousins RD.Erhard KF.Heerding DA.Keenan RM.Kwon C.Manley PJ.Newlander KA.Ross ST.Samanen JM.Uzinskas IN.Venslavsky JW.Yuan CC.-K.Haltiwanger RC.Gowen M.Hwang S.-M.James IE.Lark MW.Rieman DJ.Stroup GB.Azzarano LM.Salyers KL.Smith BR.Ward KW.Johanson KO.Huffman WF. J. Med. Chem. 2000, 43: 22 - 2b
Feuston BP.Culberson JC.Duggan ME.Hartman GD.Leu C.-T.Rodan SB. J. Med. Chem. 2002, 45: 5640 - 3
Vogt BR. inventors; US Patent 3985731. ; Chem. Abstr. 1977, 86, 55304 - 4
Vogt BR. inventors; US Patent 38875441. ; Chem. Abstr. 1975, 83, 131649 - See for example:
- 5a
Dieltiens N.Stevens CV.Masschelein K.Hennebel G.van der Jeught S. Tetrahedron 2008, 64: 4295 - 5b
Panayides J.-L.Pathak R.de Koning CB.van Otterlo WAL. Eur. J. Org. Chem. 2007, 4953 - 5c
Kogen H.Toda N.Tago K.Marumoto S.Takami K.Ori M.Yamada N.Koyama K.Naruto S.Abe K.Yamazaki R.Hara T.Aoyagi A.Abe Y.Kaneko T. Org. Lett. 2002, 4: 3359 - 6a
Walker GN. J. Org. Chem. 1972, 37: 3955 - 6b
Simchen G. Angew. Chem., Int. Ed. Engl. 1968, 7: 464 - 6c
Puar MS.Vogt BR. Tetrahedron 1978, 34: 2887 - 7
Elvidge JA.Jones DEH. J. Chem. Soc. C 1967, 2059 - 8a
Bestmann HJ.Shade G.Schmid G. Angew. Chem., Int. Ed. Engl. 1980, 19: 822 - 8b
Bestmann HJ.Shade G.Luetke H.Moenius T. Chem. Ber. 1985, 118: 2640 - For reviews, see:
- 9a
Donohoe TJ.Orr AJ.Bingham M. Angew. Chem. Int. Ed. 2006, 45: 2664 - 9b
Deiters A.Martin SF. Chem. Rev. 2004, 104: 2199 - 9c
Grubbs RH. In Handbook of Metathesis Vol. 1-3: Wiley-VCH; Weinheim: 2003. - For selected reviews, see:
- 10a
Grubbs RH.Chang S. Tetrahedron 1998, 54: 4413 - 10b
Hoveyda AH. Top. Organomet. Chem. 1998, 1: 105 - 10c
Schrock RR. Tetrahedron 1999, 55: 8141 - 10d
Phillips AJ.Abell AD. Aldrichimica Acta 1999, 32: 75 - 10e
Fürstner A. Angew. Chem. Int. Ed. 2000, 39: 3012 - 10f
Hoveyda AH.Schrock RR. Chem. Eur. J. 2001, 7: 945 - 10g
Trnka TM.Grubbs RH. Acc. Chem. Res. 2001, 34: 18 - 10h
Connon SJ.Blechert S. Angew. Chem. Int. Ed. 2003, 42: 1900 - 10i
Grubbs RH. Tetrahedron 2004, 60: 7117 - 10j
Michaut A.Rodriguez J. Angew. Chem. Int. Ed. 2006, 45: 5740 - 10k
Schrock RR. Angew. Chem. Int. Ed. 2006, 45: 3748 - 10l
Grubbs RH. Angew. Chem. Int. Ed. 2006, 45: 3760 - 11
Howe RK.Schleppnik FM. J. Heterocycl. Chem. 1982, 4: 721 - 12
Keck GE.Boden E.Sonnewald U. Tetrahedron Lett. 1981, 22: 2615 - 13
Roensch H. Eur. J. Biochem. 1972, 28: 123 - 14
Pogosyan GM.Karapetyan TG.Matsoyan SG. Armyanskii Khim. Zhur. 1971, 24: 816 ; Chem. Abstr. 1972, 76, 86171