One hundred years of benzotropone chemistry

Abstract

This review focuses on the chemistry of benzo-annulated tropones and tropolones reported since the beginning of the 20th century, which are currently used as tools by the synthetic and biological communities.

Gold‐catalyzed [4+3]‐Annulations of Benzopyriliums with Vinyldiazo Carbonyls to Form Bicyclic Heptatriene Rings with Skeletal Rearrangement

“…Compounds V‐3 and V‐4 are natural products isolated from hairy root cultures of Salvia broussonetii . Compound V‐5 is biogenetically produced on oxidation of pyrogallol; its analogues compound V‐6 is natural pigments . Compounds V‐7 are potent and specific α v integrin antagonists …”

“…Compound V‐5 is biogenetically produced on oxidation of pyrogallol; its analogues compound V‐6 is natural pigments . Compounds V‐7 are potent and specific α v integrin antagonists …”

“…We performed the reactions also the 5-phenyl derivatives 1 l-1 m (R 2 = Me and Cl), affording compounds 3 l-3 m in 79% and 76% yields respectively (entries [11][12]. For compounds have substituents at phenyl ring 1 n-1 o (R 2 = Me and Cl), their resulting product 3 n-3 o were obtained in 78% and 80% yields respectively (entries [13][14]. For 4methoxyphenyl analogue 1 p, its resulting product 3 p was obtained in 77% (entry 15).…”

Synthesis of 4,5-Benzotropone Pi-Complexes of Iron, Rhodium and Iridium and Their Potential Use in Catalytic Borrowing Hydrogen Reactions

“…Herein we report on the synthesis and characterization of rhodium, iridium and iron complexes ligated with 7H-benzo[7]annulen-7-one (4,5-benzotropone) 15 derivatives, the molecular structures of which were determined by X-ray crystallography. Moreover, some of the tropone complexes were found to catalyze the N-alkylation of aniline with benzyl alcohol via a borrowing hydrogen mechanism.…”

Biological Activity of Purpurogallin and its Derivatives

“…10,11 Dados abordados na literatura relatam que as tropolonas apresentam potencial significativo para serem inibidores potentes e seletivos para enzimas que possuem zinco como co-fator. [12][13][14][15][16] Dentre as tropolonas, destacam-se as benzotropolonas que apresentam um núcleo benzênico fundido ao anel tropolona. Esses compostos são bastante comuns no chá preto e estão geralmente presentes em cascas de árvores e galhas, frutas e folhas de chá fermentadas.…”