86673-54-3Relevant academic research and scientific papers
Fuctionalization of Linear and Angular Phenothiazine and Phenoxazine Ring Systems via Pd(0)/XPhos Mediated Suzuki-Miyaura Cross-coupling Reactions
Onoabedje, Efeturi A.,Okoro, Uchechukwu C.,Knight, David W.,Sarkar, Amitabha
, p. 1787 - 1794 (2016)
Chloro-substituted phenothiazines and phenoxazines were successfully derivatized with phenylboronic and styrylboronic acids using Suzuki–Miyaura cross-coupling reaction catalyzed by Pd(0)/XPhos for the first time in good yields. The protocol employed 4 mol% Pd and 7 mol% XPhos with K3PO4in acetonitrile at 80°C. The reaction condition is compatible with carbonyl and unprotected N–H groups in substrates. Structural assignments were established by combined spectroscopic (UV, IR,1H, and13C NMR), MS, and elemental analytical data.
Utility of Suzuki-Miyaura cross-coupling reaction in synthesis of benzo[a]phenothiazine and benzo[a]phenoxazine derivatives and their antimicrobial screening
Ayogu, Jude I.,Ezema, Benjamin E.,Ezema, Chidimma G.
, p. 4467 - 4473 (2015)
Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of 6-chloro-5H-benzo[a]phenothiazin-5-one (1), 11-amino-6-chloro-9-thio-5H-naphtho[2,1-b]pyrimido[5,4-e][1,4]oxazin-5-one (2) and 6-chloro-5H-naphtho[2,1-b]pyrido[2,3-e][1,4]oxazin-5-one (3) with phenylboronic acid and 3-nitrophenylboronic acid were thoroughly investigated. The above intermediates were prepared by the reactions of 2-aminothiophenol, 4,5-diamino-6-hydroxylpyrimidine-2-thiol and 2-aminopyridin-3-ol each with 2,3-dichloronaphthalene-1,4-dione in a basic medium using benzene/DMF as the solvent. Thereafter, each was subjected to the Suzuki-Miyaura coupling reaction with phenylboronic acid and 3-nitrophenyl boronic acid, refluxing for 7-8 h at 110 °C using tris(dibenzylideneacetone)palladium(0), dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), potassium phosphate and toluene as the catalyst, ligand, base and solvent correspondingly to yield the derivatives (1a-b), (2a-b) and (3a-b), respectively. Structures of the compounds were characterized using UV/visible spectrophotometry, FT-IR, 1H NMR and 13C NMR spectroscopy and elemental analysis. The compounds were screened against six microorganisms, viz: Bacillus subtitis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida albicans and Aspergillus niger and were shown to have significant activity against some Gram-positive micro-organisms.
