102359-91-1Relevant articles and documents
Reaction of Ninhydrin with β-Dicarbonyl Compounds
Peet, Norton P.,Huber, Edward W.,Huffman, John C.
, p. 33 - 42 (2007/10/02)
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 indenofurans.Treatment of methyl 3-aminocrotonate (2) with ninhydrin led in analogous fashion to an indenopyrrole (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.