On the mechanism of the stereo- and regioselective ether-ring opening of 1,2,3,4-tetrahydro-1β,4β-epoxy-2α,3α-carbonyldioxy arene systems with boron tribromide
✍ Scribed by Ramesh Gopalaswamy; Masato Koreeda
- Publisher
- Elsevier Science
- Year
- 1996
- Tongue
- French
- Weight
- 196 KB
- Volume
- 37
- Category
- Article
- ISSN
- 0040-4039
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N-t-Butylacetamidines 1 on heating with methyl acrylate (2) at 200˚ gave the 4,5-dihydro-3H-pyridin-2one derivatives 5. Michael addition of the acetamidines 1 as their ene-1,1-diamine tautomers 1' to 2 and the subsequent cyclization of the adducts gave derivatives 5. Amidines 1 on reaction with trim
N-t-Butylacetamidines 1 on heating with methyl vinyl ketone, acrolein or crotonaldehyde gave the 2,3-dihydropyridine derivatives 4, 5 or 6 via N-alkylation of the acetamidines 1. Reaction of amidines 1 with phenyl 1-propenyl ketone, benzalacetone or chalcone gave 3,4-dihydropyridine derivatives 8, 9
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