A novel synthetic approach for 5,6-dihydro-2,4-disubstituted-2H-2,6-methano-1,3-benzoxazocine-5-carbohydrazides 4a–j was achieved through the reaction of 1-aryl-3-(2-hydroxyphenyl)prop-2-en-1-ones 1a–c with cyanoacetohydrazones 2a,b in the presence of sufficient amount of secondary amines 3a,b. Single crystal X-ray diffraction study of 4c supports the established structure and reveals that the relative configuration is 2R,5S,6R.
MartinN., QuinteiroM., SeoaneC., and SotoJ. L., J. Org. Chem., 1990, 55, 2259.
7.
HadiA., MartinN., SeoaneC., and SotoJ. L., J. Chem. Soc. Perkin Trans., 11993, 1045.
8.
HadiA., MartinN., MendezC., QuinteiroM., SeoaneC., SotoJ. L., AlbertA., and CanoF. H., J. Chem. Soc. Perkin Trans., 11993, 1743.
9.
HadiA., MartinN., SeoaneC., SotoJ. L., AlbertA., and CanoF., J. Heterocycl. Chem., 1992, 29, 1229.
10.
Abd AllahO.A., Farmaco, 2000, 55, 641.
11.
BekhitA.A., FahmyH. T. Y., RostomS. A. F., and BarakaA. M., Eur. J. Med. Chem., 2003, 38, 27.
12.
ErianA.W., ManhiF. M., ZayedS. E., AliF. A., and ElnagdiM. H., Phosphorus, Sulfur Silicon Relat. Elem., 1998, 133, 127.
13.
RaslanM.A., Abd El-LatifF. M., OttoH. H., and SadekK. U., Org. Prep. Proc. Int., 2000, 32, 276.
14.
HusseinA.M., SherifS. M., and AtallaA. A., Monatsh. Chem., 1996, 127, 1153.
15.
HusseinA.M., Z. Naturforsch., 1998, 53b, 488.
16.
GirgisA.S., HosniH. M., and Ahmed-FaragI. S., Z. Naturforsch., 2003, 58b, 678.
17.
GirgisA.S., HosniH. M., and KalmouchA., J. Chem. Res., 2005, 38.
18.
GirgisA.S., HosniH. M., BarsoumF. F., AmerA. M. M., and Ahmed-FaragI. S., Boll. Chim. Farmac., 2004, 143, 365.
19.
GirgisA.S., KalmouchA., and HosniH. M., Amino Acids, 2004, 26, 139.
20.
GirgisA.S., IbrahimY. A., MishrikyN., LisgartenJ. N., PotterB. S., and PalmerR. A., Tetrahedron, 2001, 57, 2015.
21.
Full crystallographic details, excluding structure factors, have been deposited at Cambridge Crystallographic Data Centre (CCDC) as supplementary publication number CCDC285099.
22.
AltomareA., CascaranoG., GiacovazzoC., GuagliardiA., BurlaM. C., PolidoriG., and CamalliM., J. Appl. Cryst., 1994, 27, 435.
23.
MackayS., GilmoreC. J., EdwardsC., StewartN., and ShanklandK., maXus Computer Program for Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow1999.
24.
ElderfieldR.C., and KingT. P., J. Am. Chem. Soc., 1954, 76, 5439.
25.
RaoK.S. R. K. M., and RaoN. V. S., Indian J. Chem., 1968, 6, 66.
