Cyclizations of 2-( o -bromomethyl)benzylidene-1,3-indandione initiated by 1-benzyl-1,4-dihydronicotinamide and KCN: Selectivity of O-alkylation and C-alkylation †
1-Benzyl-1, 4-dihydronicotinamide (1) and KCN reacted with 2-(o-bromomethyl)-benzylidene-1, 3-indandione (2) to give 7, 12-dihydro-1-oxoindeno[3, 2-c][2]benzooxepine (3) and 1′-cyano-3′-hydro-2, 2′-spirobi[2H-indene]-1, 3-dione (4), respectively, and the selectivity of O-alkylation and C-alkylation is discussed.
References
1.
(a) QuayleP., Annual Reports on the Progress of Chemistry, Vol. 93, Section B, p. 92. The Royal Society of Chemistry, Cambridge1997
2.
MarshA., Annual Reports on the Progress of Chemistry, Vol. 94, Section B, p. 155. The Royal Society of Chemistry, Cambridge, 1998.
3.
For reviews on NAD(P)H models, see: (a) EisnerU., and KuthanJ., Chem. Rev, 1972, 72, 1
4.
StoutD. M., Chem. Rev., 1982, 82, 223
5.
CominsD.L., and O'ConnorS., Adv. Heterocyclic Chem, 1998, 44, 144.
6.
(a) LiuY.-C., LiB., and GuoQ.-X., Tetrahedron Lett., 1994, 35, 8429
7.
LiuY.-C., LiB., and GuoQ.-X., Tetrahedron Lett., Tetrahedron, 1995, 51, 9671
8.
ZhuX.-Q., LiuY.-C., LiJ., and WangH.-Y., J. Chem. Soc. Perkin Trans.2, 1997, 2191
9.
WangH.-Y., LiuY.-C., and GuoQ.-X., Chem. J. Chin. Univ. (submitted).
10.
(a) MolanderG.A.Acc. Chem. Res., 1998, 31, 603
11.
RousseauG., and HomsiF.Chem. Soc. Rev., 1997, 26, 453.
12.
IlluminatiG., and MandoliniL.Acc. Chem. Res, 1981, 14, 95.
13.
HobergJ.O.Tetrahedron, 1998, 54, 12631.
14.
(a) KellyT.R., OhashiN., Armstrong-ChongR. J., and BellS. H., J. Am. Chem. Soc, 1986, 108, 7100
15.
Rama RaoA.V., SinghA. K., RaoB. V., and M.K. Tetrahedron Lett, 1993, 335.
16.
WatanabeM., MorimotoH., TomadaM., and IwanagaU., Synthesis, 1994, 1083.
17.
(a) IngoldC.K.Structure and Mechanism in Organic Chemistry.Cornell University Press, Ithaca, New York, 1953, pp. 530–572.
18.
KornblumN., SmileyR. A., BlackwoodR. K., and IfflandD. C., J. Am. Chem. Soc, 1955, 77, 6296.
19.
Pearson:R.G.Hard and Soft Acids and Bases.Dowden, Hutchinson and Ross, Stroudsberg, Penn, 1973.
20.
GompperR., Angew. Chem. Int. Ed, 1964, 3, 560.
21.
LeNobelW.J., and MorrisH. F., J. Org. Chem, 1969, 34, 1969.
22.
AndersonA.G.Jr., and BerkelhammerG., J. Am. Chem. Soc., 1958, 81, 992.
