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Reactions of 4-Oxoalkanoic Acids, 4. Synthesis of (±)-6-Alkyl-5-oxa-1-azabicyclo[4.3.0]nonan-9-ones, (±)-5-Alkyl-4-oxa-1-azabicyclo[3.3.0]octan-8-ones, and Substituted 1,6-Dioxa-3,8-diazacyclodecanes by Reaction of Ethyl 4-Oxoalkanoates with 3-Aminopropanol and 2-Aminoethanol

✍ Scribed by Wedler, Christine ;Schick, Hans ;Scharfenberg-Pfeiffer, Doris ;Reck, Günter

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 432 KB
Volume: 1992
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199219920107

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✦ Synopsis

Abstract

Ethyl 4‐oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Å 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.

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