17392-15-3Relevant academic research and scientific papers
C-H bond cleavage-enabled aerobic ring-opening reaction of: In situ formed 2-aminobenzofuran-3(2 H)-ones
Jiang, Zhihong,Lao, Chichou,Wang, Yingwei,Yang, Mingrong
supporting information, p. 9448 - 9459 (2021/11/17)
A C-H bond cleavage-enabled aerobic ring-opening reaction of 2-aminobenzofuran-3(2H)-ones formed in situ by hemiacetals with a variety of amines is reported. This simple one-pot reaction provides an alternative approach to obtain o-hydroxyaryl glyoxylamides in excellent yields of up to 97%. Alkylamines react with hemiacetals via a catalyst-free dehydration condensation to generate 2-aminobenzofuran-3(2H)-ones. The in situ formed semicyclic N,O-acetals undergo the same amine-initiated C-H bond hydroxylation in air under mild conditions to afford ring-opening products. Similarly, arylamines were investigated as substrates for a two-step tandem process involving a DPP-catalyzed condensation followed by a Et2NH-mediated C-H hydroxylation. Unlike the previously reported functionalization of N,O-acetals via a C-O or C-N cleavage, the aerobic oxidative C-H hydroxylation in this reaction, which is promoted by using stoichiometric amounts of alkylamines as both a Lewis base and a reductant at room temperature under atmospheric air, proceeds via α-carbonyl-stabilized carbanion intermediates from the C-H cleavage of N,O-acetals. This journal is
Highly efficient heterogeneous V2O5@TiO2 catalyzed the rapid transformation of boronic acids to phenols
Upadhyay, Rahul,Singh, Deepak,Maurya, Sushil K.
supporting information, p. 3925 - 3931 (2021/08/24)
A V2O5@TiO2 catalyzed green and efficient protocol for the hydroxylation of boronic acid into phenol has been developed utilizing environmentally benign oxidant hydrogen peroxide. A wide range of electron-donating and the electron-withdrawing group-containing (hetero)aryl boronic acids were transformed into their corresponding phenol. The methodology was also applied successfully to transform various natural and bioactive molecules like tocopherol, amino acids, cinchonidine, vasicinone, menthol, and pharmaceuticals such as ciprofloxacin, ibuprofen, and paracetamol. The other feature of the methodology includes gram-scale synthetic applicability, recyclability, and short reaction time.
Logical design and synthesis of indole-2,3-diones and 2-hydroxy-3(2H)- benzofuranones via one-pot intramolecular cyclization
Gao, Fang-Fang,Xue, Wei-Jian,Wang, Jun-Gang,Wu, An-Xin
, p. 4331 - 4335 (2014/06/10)
A novel and attractive protocol to synthesis indole-2,3-diones and 2-hydroxy-3(2H)-benzofuranones and via copper(II) oxide catalyzed intramolecular cyclization is described. This method possesses functional-group compatibility, easy workup procedure, shorter reaction time and high yields.
Oxidation of Furan, Pyrrole, Thiophene, Benzo furan, and Benzothiophene with Oxodiperoxomolybdenum (VI), MoO5*HMPA
Chien, Chun-Sheng,Kawasaki, Tomomi,Sakamoto, Masanori
, p. 5071 - 5074 (2007/10/02)
The oxidation of 2,5-diphenylfuran (1) with (hexamethylphophoramide)oxodiperoxomolybdenum(VI), MoO5*HMP, gave cis-1,4-diphenyl-2-butene-1,4-dione (2) and its cis-epoxide 3. 2,3-Diphenylpyrrole (4) was similarly treated with MoO5*HMPA to give the dimeric product 6, together with the cis-epoxide 3 and the trans-olefin 5.In the case of 2,5-diphenylthiophene (8), the oxidation with MoO5*HMPA occurred at the sulfur atom of 8 to give thiophene 1,1-dioxide (9).The oxidation of benzofuran (10) and benzothiophene (16) with MoO5*HMPA is also described.Keywords: furan; pyrrole; thiophene; benzofuran; benzothiophene; peroxomolybdenum complex; oxidation; epoxidation; dimerization
