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Studies of bioactive heterocycles: amino Claisen rearrangement of 4-N-(4-aryloxybut-2-ynyl),N-methylaminocoumarins

✍ Scribed by K.C Majumdar; T Bhattacharyya

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
95 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

Thermal amino-Claisen rearrangement of 4-N-(aryloxybut-2-ynyl),N-methyl-aminocoumarins (8a-e) in refluxing odichlorobenzene gave 4-aryloxymethylene-1-methyl-1,2,3-trihydropyrido[3,2-c][1]benzopyran-5-ones (9a-e) in 56-72% isolated yields. Substrates (8a-f) were prepared from 4-chlorocoumarin (6a,b) and N-(4-ary-loxybutynyl),N-methylamine (7a-f) in 68-77% yields.

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A number of 4-N-(4%-aryloxybut-2%-ynyl),N-methylaminocoumarins (4a-e) on treatment with one equivalent of 3chloroperoxybenzoic acid at 0-5Β°C for 10 min and then stirring at rt for 10 h afforded pyrrolo[3,2-c]coumarin derivatives in 70-75% yields. The 4-N-(4%-aryloxybut-2%-ynyl),N-methylaminocoumarin