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- Title
Undec-10-enal in the Synthesis of Undec-10-enyl Undec-10-enoate and O- and N-containing Macroheterocycles.
- Authors
Mingaleeva, G. R.; Yakovleva, M. P.; Ishmuratov, G. Yu.
- Abstract
An effective synthesis of four potentially biologically active O- and N-containing 23-, 28-, 30-, and 31-membered macroheterocycles from undec-10-enal was carried out. First, undec-10-enal was converted to undec-10-enyl undec-10-enoate via the Tishchenko disproportionation reaction catalyzed by Al(i-PrO)3. The subsequent Wacker–Tsuji oxidation of undec-10-enyl undec-10-enoate gave 10-oxoundecanyl 10-oxoundecanoate. Finally, the [1+1]-condensation of 10-oxoundecanyl-10-oxoundecenoate with hydrazine hydrate or malonic, glutaric, or adipic acid dihydrazides resulted in the synthesis of four macroheterocycles.
- Subjects
ADIPIC acid; HYDRAZINES; OXIDATION; HYDRAZINE
- Publication
Russian Journal of Organic Chemistry, 2024, Vol 60, Issue 2, p206
- ISSN
1070-4280
- Publication type
Article
- DOI
10.1134/S1070428024020040