Revival of troponoid chemistry

Abstract

He was born in Carrara and did his university study at the University of Padua, where he also did postdoctoral research with Antonino Fava. He was for several years at the University of Pisa, where he carried out most of his work on aromatic substitution, catalytic phenomena, bridged polycyclics, and troponoids, as well as at the University of Catania. He was also at the Gorlaeus Laboratorla, Leiden, and at Imperial College, London.

New method for the synthesis of β-tropolones: Structures of condensation products of o-quinones with 2-methylquinolines and the mechanism of their formation

“…and their synthetic analogs have at tracted considerable attention. 1 Most of the already known tropolones belong to α tropolones, i.e., 2 hydroxy tropone derivatives. β Tropolones (3 hydroxytropones) are much less studied, although they include biologically active compounds, such as stipitatic acid (1) and puberu lic acid (2).…”

Prototropic tautomerism and solid-state photochromism of N-phenyl-2-aminotropones

“…As a new candidate for such photosensitive organic chromophores based on prototropic tautomerism, we focused our interest on 2-hydroxytropone (tropolone) derivatives. Since their discovery, tropolone natural products and synthetic tropolone derivatives have attracted considerable interest due to the unique structure and properties of the tropolone ring [12,13]. Tropolone undergoes a proton tunneling from hydroxyl group to carbonyl oxygen atom [14,15].…”

Synthesis of ß-tropolone and fused heterocycle derivatives by acid-catalyzed and photoreactions of o-quinones with quinolines and benzimidazoles

“…2-hydroxytropones, whereas β-tropolones (3-hydroxytropones) have hitherto received much less attention, even though such biologically active products as stipitatic (2,6-dihydroxy-4-carboxytropone) and puberulic (2,3,7-trihydroxy-5-carboxytropone) acids, which are mould metabolites of Penicillium family, may be equally assigned to both α-and β-tropolone derivatives. 1 The principal reason for this is the lack of expedient methods for the synthesis of derivatives of β-tropolones. A general approach to β-tropolones is based on the multistep transformation that starts from the reduction of 3,4,5-trimethoxybenzoic acid to 3,5-dimethoxy-1,4-dihydrobenzylic alcohol followed by thermal expansion of the six-membered ring of its tosyl ester to give a mixture of 1,3-dimethoxycycloheptatrienes and the subsequent oxidation of the latter.…”