Journal
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 57, Issue 10, Pages 1643-1649Publisher
MAIK NAUKA/INTERPERIODICA/SPRINGER
DOI: 10.1134/S1070428021100122
Keywords
2,3-dibromopropanamides; potassium tert-butoxide; 2-methylidene-beta-lactams; beta-bromomethacryl-amides; azetidin-2-ones
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Funding
- [AAAA-A20-120012090021-4]
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The study investigated the transformations of 2,3-dibromo-2-methylpropanamides with different substituents on the nitrogen atom by potassium tert-butoxide in THF. Results showed that the amount of t-BuOK significantly affected the yield and selectivity of the products.
2,3-Dibromo-2-methylpropanamides with different substituents on the nitrogen atom were synthe-sized, and their transformations by the action of potassium tert-butoxide in THF were studied. 2,3-Dibromo-N-(4-methoxyphenyl)-2-methylpropanamide and 2,3-dibromo-N-(2,5-dibromo-4-methoxyphenyl)-2-methyl-propan-amide reacted with 1-2 equiv of t-BuOK to give the corresponding N-substituted 3-bromo-3-methyl- and 3-methylideneazetidin-2-ones with acceptable yields and selectivity. Increase of the amount of t-BuOK to 3-5 equiv led to significant reduction of the yield of vinyl bromides and 3-methylideneazetidin-2-ones. On the other hand, the reaction of 2,3-dibromo-N-(tert-butyl)-2-methylpropanamide with t-BuOK afforded 3-(tert-bu-toxymethyl)-1-tert-butylazetidin-2-one with a good yield and selectivity.
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