Metal Catalyzed Synthesis and Antimicrobial Studies of some New Amido Derivatives of Non-Linear Polycyclic Diazaphenothiazinone
synthesis, arylation, amido derivatives and palladium catalysis
Abstract
The synthesis of novel non-linear polycyclic diazaphenothiazine and its amido derivatives via Buchwald -Hartwig reaction protocol is reported. By reacting 2-amino-5bromopyrazine-3[4H]-thione and 2, 3-dichloro-1, 4-naphthoquinone in the presence of anhydrous sodium carbonate, 9-bromo-6-chloro-8, 11-daiza-5H-benzo[a] phenothiazin-5-one was obtained. The arylation of 9-bromo-6-chloro-8, 11-daiza-5H-benzo[a]pheno-thiazin-5-one with some amides under palladium catalysis gave the amido derivatives in good yield. The stability of these cyclic quinoneimine systems, which has been attributed to ionic resonance effect, is noted. Structural assignments were based on UV, IR and NMR spectra as well as elemental analysis. These compounds showed significant antimicrobial activity against E. coli, Staphylococcus spp, Bacillus spp. and Pseudomonas aeruginosa at varying concentrations.
Downloads
How to Cite
References
P Evans (2006) Metal catalyzed cascade reactions (Topics in organometalic chemistry. 19.
Irina Beletskaya (2002) Transition metal-catalyzed reactions in heterocyclic chemistry. 74(8), 1327-1337.
Zhong‐xia Wang, Ning Liu (2012) Nickel‐Catalyzed Cross‐Coupling with Pincer Ligands. 2012(6), 901-911.
P Liu (2010) Theoretical studies of transition metalcatalyzed organic reactions.
Ei‐ichi Negishi (2011) Transition Metal Catalyzed Organometallic Reactions that Have Revolutionized Organic Synthesis. 38(22).
Zhaoqing Xu, Ei-Ichi Negishi (2008) Efficient and Stereoselective Synthesis of Yellow Scale Pheromone via Alkyne Haloboration, Zr-Catalyzed Asymmetric Carboalumination of Alkenes (ZACA Reaction), and Pd-Catalyzed Tandem Negishi Coupling. 10(19), 4311-4314.
J Harting (2002) Handbook of Organopalladium Chemistry for Organic Synthesis. 1, 1051-1096.
A Davies (1998) Book review: Metal-catalyzed cross-coupling reactions. F. Diederich and P. J. Stang (eds) Wiley-VCH, Weinheim, 1998. xxi + 517 pages, �85 ISBN 3-527-29421-X. 12(12), 878-878.
De Majere, F Diederick (2004) Metal catalyzed crosscoupling Reactions. 1, 213.
F; Bellina, R Rossi (2009) Recent Advances in the Synthesis of (Hetero) Aryl-Substituted Heteroarenes via Transition Metal-Catalyzed Direct (Hetero) Arylation of Heteroarenes C-H Bonds with Aryl Halides or Pseudohalides, Diaryliodonim Saltsand Potassium Aryltrifluoroborates. 893, 10269-10310.
M Ezeokonkwo, F Ugwuona, I Ugwu (2015) Synthesis and Antibacterial Studies of Some Alkynylated Benzo[a]phenoxazin-5-one and 1,4-Naphthoquinone Derivatives. 27(10), 3843-3850.
K Shaughnessy (2011) Identification of a Nitrenoid Reductive Elimination Pathway in Nickel-Catalyzed CN Cross-Coupling.
W Akinriboya (2010) Nobel Prize for Chemistry Awarded to Three Scientists. 1(3), 28-29.
Samir Messaoudi, Davide Audisio, Jean-Daniel Brion, Mouâd Alami (2007) Rapid access to 3-(N-substituted)-aminoquinolin-2(1H)-ones using palladium-catalyzed C-N bond coupling reaction. 63(41), 10202-10210.
E Godwin-Nwakwasi, U Okoro, A Ijeomah, I Agbo, M Ezeokonkwo (2017) Palladium Catalyzed Transformation and Antimicrobial Screening of Novel Angular Azaphenothiazines. 29(4), 742-748.
Charles Okafor (1967) Heterocyclic series. I. A novel diazaphenothiazine system. 32(6), 2006-2007.
U Okoro, M C; Nnabugwu, C Nwadinigwe (2008) ChemInform Abstract: Synthesis of New Triaza and Tetraaza Analogues of Phenothiazine.. 21(21), 171-180.
Charles Okafor, Uche Okoro (1991) New non-linear polycyclic azaphenothiazine dyestuffs. 16(2), 149-163.
A Ijeomah, U O; Okoro, C; Godwin-Nwakwasi, E Chah, K (2014) The Synthesis, Characterization and Antimicrobial Screening of 8-Amino-6-Chloro-1,9,11-Triazabenzo[a]Phenothizin-5-one. 3(12), 3-14.
Okorou, A Ijeomah (2006) Synthesis of New Non-linear Polycyclic Diazaphenothizine Ring System. 16(4), 245-250.
Charles Okafor (1985) New phenothiazine dyes and pigments. 6(6), 405-415.
Charles Okafor, Uche Okoro (1988) A new synthesis of 'three-branched' diazaphenothiazine dyes. 9(6), 427-442.
F; Ozawa, A; Kubo, T Hayashi (1992) Generation of Tertiary Phosphine Co-ordinated Pd (0) Species from Pd(OAc) 2 in the Catalytic Heck Reaction. 2177-2180.
B Fors, P; P; Krattiger, E; Strieter, S Buchwald (2008) Water-Mediated Catalyst Preactivation: An Efficient Protocol in C-N Cross-Coupling Reactions. 10(16), 3505-3508.
Alex Muci, Stephen Buchwald (2002) Practical Palladium Catalysts for C-N and C-O Bond Formation. 219, 131-209.
Sasmita Mohanty, D; Suresh, Maravanji Balakrishna, Joel. Mague (2008) An inexpensive and highly stable ligand 1,4-bis(2-hydroxy-3,5-di-tert-butylbenzyl)piperazine for Mizoroki-Heck and room temperature Suzuki-Miyaura cross-coupling reactions. 64(1), 240-247.
C; Perez, M; Pauli, P Bazerque (1990) Supplemental Information 2: Agar well diffusion assay.. 15, 113-115.
(2002) Performance standards for Antimicrobial Disc Dilution Susceptibility Tests for Bacteria isolated from. 22, 13-14.
R Vardanyan, V Hruby (2006) Antihistamine Drugs. 219-235.
Published
2019-06-25
Issue
Section
License
Copyright (c) 2019 Authors and Global Journals Private Limited
This work is licensed under a Creative Commons Attribution 4.0 International License.