Acetals of lactams and acid amides. 51. Cyclization of α-cyano-Β-phenylamino-N-dimethylaminomethyleneacrylamide to pyrimido[5,4-c]quinol-4-one
✍ Scribed by L. V. Ershov; N. Z. Tugusheva; V. G. Granik
- Publisher
- Springer US
- Year
- 1988
- Tongue
- English
- Weight
- 252 KB
- Volume
- 24
- Category
- Article
- ISSN
- 0009-3122
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✦ Synopsis
N-Acetyl-2-(p-phenetidino)-3-cyano-5.~6~7,8-tetrahydroquinoline (lllg). A mixture of 1.92 g (0.01 mole) of (I) and 0.01 mole of N-acetyl-p-phenetidine was heated for 6 h at 190~ treated with hot water, and the solid filtered off and crystallized from ethanol to give 1.21 g (63%) of product, mp I15-I17~ Found: C 71.7; H 6.2; N 12.4%. C2oH2:N302. Calculated: C 71.6; H 6~ N 12o5%.
Similarly, the nitrile (I) and acetanilide gave 76% of (IIIa). A mixed melting point with (IIIa) obtained from (IIa) and acetic anhydride gave no depression.
2-Substituted l-Aryl-6~7~8,9-tetrahydropyrimido[4~5-b]quinolin-4-ones (IVa-f). Dry hydrogen chloride was passed for 3 h into a solution of 0o01 mole of (IIIa-f) in 40 ml of anhydrous ethanol, and the solid which separated was filtered off, treated with aqueous sodium acetate, and crystallized from ethanol to give (IVa-f). i.