Synthesis of dibenzo derivatives of (4-oxotetrahydropyrano)oxa-14-crown-4 and 1,4,7-trioxacyclohexadeca-8,10,13,15-tetraen-12-one. Transformation of the latter into (4-oxopiperidino)aza-14-crown-4

• Published in: Russian journal of organic chemistry Vol. 44; no. 3; pp. 462 - 464
• Main Authors: Le An', Tuan, Levov, A. N, Soldatenkov, A. T, Gruzdev, R. D, Khieu, Chyong Khong
• Format: Journal Article
• Language: English
• Published: Dordrecht Dordrecht : SP MAIK Nauka/Interperiodica 2008; SP MAIK Nauka/Interperiodica
• Subjects: Chemistry; Chemistry and Materials Science; Organic Chemistry; Diethyl Ketone; Methylamine; Gaseous Ammonia; Acetic Acid Lead; Crown Ether
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S107042800803024X

The reaction of diethyl ketone with 2-{2-[2-(2-formylphenoxy)ethoxy]ethoxy}benzaldehyde in acid medium at room temperature gave 43% of dibenzo(4-oxotetrahydropyrano)oxa-14-crown-4. The condensation of the same compounds in boiling ethanol in the presence of alkali involved cascade transformations leading to the formation of thermody namically more stable dibenzocrownophane which was assigned the structure of 8,9:15,16-dibenzo-1,4,7-trioxacyclohexadec-8,10,13,15-tetraen-12-one (yield 29%). Treatment of an alcoholic solution of the latter with gaseous ammonia or methylamine at 20°C afforded 73-74% of dibenzoaza-14-crowns-4 containing a 4-oxopiperidine fragment.