Ring-Closing Metathesis Approach
to 2H-2-Benzazepine-1,3-diones

Stéphane Lebrun; Axel Couture; Eric Deniau; Pierre Grandclaudon

doi:10.1055/s-0030-1258416

PAPER

Ring-Closing Metathesis Approach to 2H-2-Benzazepine-1,3-diones

Stéphane Lebrun^a,b, Axel Couture*^a,c, Eric Deniau^a,b, Pierre Grandclaudon^a,b
^a Université Lille Nord de France, 59000 Lille, France
Fax: +33(3)20436309; e-Mail: axel.couture@univ-lille1.fr;
^b USTL, Laboratoire de Chimie Organique Physique, EA CMF 4478, Bâtiment C3(2), 59655 Villeneuve d’Ascq Cedex, France
^c CNRS, UMR 8181 ‘UCCS’, Bâtiment C3(2), 59655 Villeneuve d’Ascq Cedex, France

Abstract

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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

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References

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