The reaction of diethyl oxalate with ethereal oxygen-containing diamines under high-dilution conditions gave 2 : 2 reaction products, 22-, 28-, and 34-membered macrocyclic amides in good yields. From the 2 : 1-mixed reaction between diethyl oxalate and the diamines, acyclic 2 : 1 and 3 : 2 reaction products were isolated at a ratio of ca. 9 : 1. The intermediate 2 : 1 and 3 : 2 reaction products led to the 2 : 2 reaction products mentioned above and the 3 : 3 reaction products, 33-, 42-, and 51-membered macrocyclic amides, respectively, upon reaction with additional corresponding diamines. Also, other macrocyclic amides were synthesized by combining the 2 : 1 reaction products and diamines.
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