A facile and environmentally benign synthesis of 2H-benzo[b] [1,4] oxazines of potential biological importance

被引:2
作者
Zhimomi, Betokali K. [1 ]
Imchen, Putusenla [1 ]
Phom, Manthae [1 ]
Achumi, Phitovili [1 ]
Tumtin, Shokip [2 ]
Swu, Toka [3 ]
Phucho, Tovishe [1 ]
机构
[1] Nagaland Univ, Dept Chem, Zunheboto 798627, Nagaland, India
[2] Fazl Ali Coll, Dept Chem, Mokukchung 798601, Nagaland, India
[3] Pondicherry Univ, Dept Chem, Pududcherry 605014, India
关键词
Oxazine; catalyst; microwave; antibacterial; antioxidant; ONE-POT SYNTHESIS; ANTIMICROBIAL ACTIVITY; HYDROXAMIC ACIDS; DERIVATIVES; DESIGN; INHIBITORS; ANTIOXIDANTS;
D O I
10.24820/ark.5550190.p012.205
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient microwave-assisted protocol is reported for the synthesis of fifteen 2H-benzo[b] H-benzo[b] [1,4] oxazine from phenacylbromides and aminophenols using Cs2CO3 2 CO 3 as a base catalyst, out of which four compounds were found to be novel. The method gave 70 to 86% yields in 3-5 minutes. Microwave assistance proved to have reduced the reaction time, improved the yield, purity, and made the work-up easier. Characterization was done by FT-IR, 1 HNMR, 13 CNMR, and mass spectrometric analysis. The in vitro antibacterial and in vitro antioxidant properties of the synthesized oxazines were assessed. The results suggested that they possess good antibacterial and antioxidant activity. The compound 3h having chlorine and methyl as substituents exhibits higher antibacterial activity with inhibition zones of 14-19mm. The compound 3d having methoxy and methyl as substituents showed high antioxidant activity with IC50 50 value of 53.33(mu g/ml).
引用
收藏
页数:14
相关论文
共 37 条
[1]   Design and synthesis of boron containing 2,4-disubstituted-phthalazin-1(2H)-one and 3,7-disubstituted-2H-benzo[b][1,4] oxazine derivatives as potential HGF-mimetic agents [J].
Das, Bhaskar C. ;
Tang, Xiang-Ying ;
Sanyal, Swarnava .
TETRAHEDRON LETTERS, 2011, 52 (33) :4292-4294
[2]   Design, synthesis and biological evaluation of 2H-benzo[b][1,4] oxazine derivatives as hypoxia targeted compounds for cancer therapeutics [J].
Das, Bhaskar C. ;
Madhukumar, Ankanahlli V. ;
Anguiano, Jaime ;
Mani, Sridhar .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) :4204-4206
[3]  
Ding CJ, 2009, CHEM RES CHINESE U, V25, P174
[4]   Synthesis and reactivity of enaminone of naphtho[b]1,4-oxazine: One pot synthesis of novel isolated and heterocycle-fused derivatives with antimicrobial and antifungal activities [J].
El Azab, Islam H. ;
Khaled, Khaled M. .
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2015, 41 (04) :421-436
[5]  
Elavarasan S., 2013, IJPMC, V6, P131, DOI [10.1155/2013/640936, DOI 10.1155/2013/640936]
[6]   A Review on Current Synthetic Strategies of Oxazines [J].
Gaonkar, Santosh L. ;
Nagaraj, Vignesh U. ;
Nayak, Swarnagowri .
MINI-REVIEWS IN ORGANIC CHEMISTRY, 2019, 16 (01) :43-58
[7]   SYNTHESIS AND ANTIBACTERIAL ACTIVITIES OF OPTICALLY-ACTIVE OFLOXACIN [J].
HAYAKAWA, I ;
ATARASHI, S ;
YOKOHAMA, S ;
IMAMURA, M ;
SAKANO, KI ;
FURUKAWA, M .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1986, 29 (01) :163-164
[8]  
Hayes BL, 2004, ALDRICHIM ACTA, V37, P66
[9]   IN-VITRO AND IN-VIVO ACTIVITIES OF THE BENZOXAZINORIFAMYCIN KRM-1648 AGAINST MYCOBACTERIUM-TUBERCULOSIS [J].
HIRATA, T ;
SAITO, H ;
TOMIOKA, H ;
SATO, K ;
JIDOI, J ;
HOSOE, K ;
HIDAKA, T .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1995, 39 (10) :2295-2303
[10]   Recent advances in the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones and 3,4-dihydro-2H-1,4-benzoxazines [J].
Ilas, J ;
Anderluh, PS ;
Dolenc, MS ;
Kikelj, D .
TETRAHEDRON, 2005, 61 (31) :7325-7348