C. Wedler, H. Schick, D. Scharfenberg-Pfeiffer
Jan 13, 1992
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0
Influential Citations
4
Citations
Journal
European Journal of Organic Chemistry
Abstract
Ethyl 4-oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 A in almost quantitative yield with 3-aminopropanol and 2-aminoethanol to form the bicyclic lactams rac-2 and rac-3, respectively. Surprisingly, the (±)-5-alkyl-4-oxa-1-azabicyclo[3.3.0]octan-8-ones rac-3a–d dimerize in trichloromethane saturated with 2 N HCl to the ten-membered heterocycles 4a–d. The structures of the substituted 1,6-dioxa-3,8-diazacyclodecanes 4a and 4c have been determined by an X-ray crystal analysis.