Unprecedented synthesis of a novel amino quinone ring system via oxidative decarboxylation of quinone-based α,α-amino esters

Abstract

An unusual and efficient method for the synthesis of new quinone-based amine and its derivatives from the corresponding alpha,alpha-amino ester is described. The procedure involves the quinone-based system's oxidative decarboxylation via hydride transfer throughout basic hydrolysis. This synthetic method provides, with good yields, rapid access to new potentially cytotoxic quinones.

Dihydrithieno[2,3-b]naphto-4,9-dione analogues as anticancer agents: Synthesis and in cell pharmacological studies

“…Initially, direct amidation using the Curtius rearrangement upon derivatization of the ester to acylazide [26] and sodium methoxide catalyzed transamidation [27], was unsuccessful. On the other hand, hydrolysis of the ester prior to amidation was not feasible due to rapid decarboxylation in both acidic and alkaline media, as previously described [28]. Consequently, we used a different synthetic route given the feasibility of a solid phase catalysed double Michael addition to quinone systems, previously reported [25].…”

Design, Synthesis, and Cytotoxic Evaluation of Acyl Derivatives of 3-Aminonaphtho[2,3-b]thiophene-4,9-dione, a Quinone-Based System

“…The condensation of 9, obtained after deprotection of the corresponding N-Boc TNQ (14) using 50% TFA in dichloromethane, 18 with chloroacethyl chloride afforded the (2 0 -chloro)acetamide intermediate 15 (88% yield). Reaction of 15 with diethylamine in THF and triethylamine at reflux afforded the final derivative 11k.…”

Synthesis of mitomycin analogs catalyzed by coupling of laccase with lipase and the kinetic model

“…Mitomycin C (MMC) is an important member of mitomycins, however, the serious adverse effects resulting from its high toxicity has limited its clinical application to a large extent . Until now, the conventional chemical catalysis for synthesis of mitomycins still fails to reach an excellent yield as well as environmental friendliness . Because of the high selectivity of enzymes, milder reaction conditions, and lack of toxicity, enzymatic processes are attracting more and more attention …”