108164-13-2Relevant articles and documents
Furan and Pyrrole Formation from 2-Nitro-1-phenylpropene and Acetoacetic Esters
Gomez-Sanchez, Antonio,Fernandez-Fernandez, Rosario,Pascual, Conrado,Bellanato, Juana
, p. 2701 - 2713 (2007/10/02)
Methyl acetoacetate and 2-nitro-1-phenylpropene react to yield an adduct formulated as 5-methoxycarbonyl-3,6-dimethyl-4-phenyl-5,6-dihydro-4H-1,2-oxazine-2-oxide (6B).This compound is very reactive and is transformed, upon dissolution in dimethyl sulphoxide, into a mixture of methyl 2-acetyl-4-nitro-3-phenylpentanoate (6C) and methyl 2,5-dimethyl-4-phenyl-3-furoate (3a).Dissolution of (6B) in chloroform brought about its conversion into methyl 2-acetyl-4-oxo-3-phenylpentanoate (4a).Treatment of (6B) with F3B:OEt2 in ether produced the diketone (4a) and methyl 1-hydroxy- 2,5-dimethyl-4-phenylpyrrole-3-carboxylate (11); and treatment of (6B) with hydrogen chloride in ether afforded the furoic ester (3a), the diketone (4a), and the 1-hydroxypyrrole (11).The reaction of (6B) with methylamine gave methyl 4,5-dihydro-2,5-dimethyl-5-methylazo-4-phenylfuran-3-carboxylate (9) and methyl 1,2,5-trimethyl-4-phenylpyrrole-3-carboxylate (12); the former compound could be quantitatively converted into the pyrrole (12) by treatment with an excess of methylamine.
