2-(1-Methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one: Acid-catalyzed isomerization of the Z isomer to the E isomer
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چکیده
Crystals of (Z )-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2]octan-3-one (I) were obtained from a condensation reaction of 1-methyl-1H-indole-3-carboxaldehyde with 1-aza-bicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The isomeric (E)-2-(1-methyl-1H-indol-3-ylmethylene)-1-aza-bicyclo[2.2.2] octan-3-one hydrochloride (II) was obtained by treating a methanolic solution of I with a 1M solution of hydrogen chloride diethyl ether, followed by crystallization of resultant product from methanol. Crystal data: I, is monoclinic, P21, a = 5.7440(10), b = 11.102(2), c = 10.708(2) Å, β = 91.751(10)◦, and V = 682.5(2) Å3 with Z = 2, for Dcal = 1.296 mg/m3 and II, is monoclinic, P21/c, a = 8.8510(2), b = 17.4990(5), c = 20.4300(5) Å, β = 101.3620(12)◦, V = 3102.26(14) with Z = 8, for Dcal = 1.316 mg/m3.
منابع مشابه
(Z)-2-(1-Phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-one and (Z)-(S)-2-(1-phenylsulfonyl-1H-indol-3-ylmethylene)-1-azabicyclo[2.2.2]octan-3-ol.
The title compounds, C22H20N2O3S, (I), and C22H22N2O3S, (II), crystallize in space groups P-1 and P2(1)2(1)2(1), respectively. The indole rings are planar and the benzene ring of the phenylsulfonyl group makes a dihedral angle with the mean plane of the indole ring of 90.2 (2) degrees in (I) and 94.0 (2) degrees in (II). In both molecules, the double bond connecting the aza-bicyclic and indole ...
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