A facile method for the synthesis of thiocoumestan derivatives

Abstract

in Wiley InterScience (www.interscience.wiley.com).An efficient synthesis of thiocoumestan derivatives, starting from catechols and 4-mercaptocoumarin in the presence of potassium ferricyanide as an oxidizing agent (Decker oxidation) was developed. The results indicate that the 4-mercaptocoumarin participates in Michael addition reactions with in situ generated o-benzoquinones. The present work has led to the development of a one-pot oxidative method for the synthesis of the 6H-benzothieno[3,2-c][1]benzopyron-6-one derivatives.

Chemical and Electrochemical Syntheses of Benzo[b](1,4)‐diazepine‐7,8‐diones

“…We showed before that K 3 Fe(CN) 6 can be used as a good oxidative reagent for the chemical oxidation of catechols [7]. The chemical synthesis with K 3 Fe(CN) 6 was fast, and the reaction completed in 15 min.…”

“…In continuation to our studies on the synthesis of new heterocyclic compounds [6][7][8][9][10][11][12][13][14][15][16][17][18], we would like to report the synthesis of different, new benzodiazepinediones (7a-f) from the reaction of catechols (1a-c) with N,N 0 -dimethylpropylenediamine (3a) and N,N 0 -diethylpropylenediamine (3b) via both the chemical (K 3 Fe(CN) 6 as an oxidant) [7] and electrochemical syntheses in the phosphate buffer solution (PBS) (Scheme 1).…”

Insight on Mercapto-Coumarins: Synthesis and Reactivity

“…Through an EC mechanism and in a one-pot process, 4-(dihydroxyphenylthio)-2 H -chromen-2-one derivatives 29a and 29b were afforded ( Scheme 12 ) [ 34 ]. In another work of the same group, they explored the reactivity of catechol ( 28 ) and 4-mercapto-coumarin ( 14 ) in the presence of potassium ferricyanide as an oxidizing agent (decker oxidation) to develop thieno[3,2-c]chromen-6-onederivatives ( 30 ) ( Scheme 12 ) [ 35 ].…”

Efficient synthesis of 4-sulfanylcoumarins from 3-bromo-coumarinsviaa highly selective DABCO-mediated one-pot thia-Michael addition/elimination process

“…In addition, elemental sulfur, inorganic sulfides, KSCN, CS 2 and thiourea have also served as sources of the sulfur atom, 6 c ,8 b ,10 whereas the alkylation of the resulting 4-mercaptocoumarins 11 and their arylation through the use of electrochemical means 12 have been disclosed as other options.…”