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Reaction of ninhydrin with β‐dicarbonyl compounds
Author(s) -
Peet Norton P.,
Huber Edward W.,
Huffman John C.
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320106
Subject(s) - ninhydrin , chemistry , adduct , pyrrole , medicinal chemistry , organic chemistry , tricyclic , stereochemistry , amino acid , biochemistry
The reactions of ninhydrin ( 1 ) with β‐ketoesters and β‐diketones were studied. Two kinds of products were observed, which were either simple adducts of the dicarbonyl compounds to the center carbonyl group of ninhydrin, or tricyclic indeno[1,2‐ b ]furans. Treatment of methyl 3‐aminocrotonate ( 2 ) with ninhydrin led in analogous fashion to an indeno[1,2‐ b ]pyrrole ( 3 ) which was reduced to a complex tetracyclic dihydropyridine 12 . A mechanism for the production of 12 is presented. Structures for the novel heterocycles are supported by high resolution nmr studies and X‐ray crystallography.