6,7,8,9-Tetrahydro-3-methyl-1H-pyrano[4,3-b]quinolin-1-one

• Published in: Acta crystallographica. Section C, Crystal structure communications Vol. 55; no. 10; pp. 1698 - 1701
• Main Authors: Hua, D. H., Chen, Y., Sin, H.-S., Robinson, P. D., Meyers, C. Y., Perchellet, E. M., Perchellet, J.-P., Chiang, P. K., Biellmann, J.-F.
• Format: Journal Article
• Language: English
• Published: 5 Abbey Square, Chester, Cheshire CH1 2HU, England International Union of Crystallography 15.10.1999; Blackwell
• Subjects: Aldehyde Reductase - antagonists & inhibitors; Cholinesterase Inhibitors - chemistry; Condensed matter: structure, mechanical and thermal properties; Crystallography, X-Ray; Enzyme Inhibitors - chemistry; Exact sciences and technology; Heterocyclic compounds; Humans; Molecular Structure; Organic compounds; Physics; Pyrans - chemistry; Quinolines - chemistry; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; Molecular structure; XRD; Tricyclic compound; Experimental study; Organic compounds; Oxygen nitrogen heterocycle; Lactones; Crystal structure
• ISSN: 0108-2701; 1600-5759
• DOI: 10.1107/S0108270199007301

The condensation reaction of 4-amino-6-methyl-2-pyrone with 1-cyclohexenecarboxaldehyde and a catalytic amount of (S)-(+)-10-camphorsulfonic acid in toluene at 358 K gave a 1:2.5 ratio of the title compound, (1) (C13H13NO2), and 7,8,9,10-tetrahydro-1H-pyrano[4,3-c]isoquinoline-1-one, (2). The formation of (2) presumably proceeds through an intermediate imine. Both (1) and (2) show inhibitory activities against acetylcholinesterase and human aldose reductase. Of the three linear-fused rings of (1), both ring A and ring B are planar and the angle between these planes is 0.46 (13) degrees. While the two C atoms of cyclohexane ring C attached to its common atoms with ring B are in the plane of the latter, as expected, the remaining two C atoms of ring C are out of this plane, by 0.342 (4) and -0.402 (3) A, respectively.