Microwave assisted synthesis and antibacterial study of 2-aryl-1,3-benzoxathiin-4-ones

doi:10.3969/j.issn.1000-1565.2016.04.011

Journal of Hebei University (Natural Science Edition) ›› 2016, Vol. 36 ›› Issue (4): 396-401.DOI: 10.3969/j.issn.1000-1565.2016.04.011

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Microwave assisted synthesis and antibacterial study of 2-aryl-1,3-benzoxathiin-4-ones

FENG Junna^1,2,PENG Shaohui³,CUI Penglei^1,4,CHEN Hua¹,LI Xiaoliu¹

1.Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China; 2.School of Earth Science and Resources, China University of Geosciences Great Wall College, Baoding 071000, China; 3.School of Foreign Languages, China University of Geosciences Great Wall College, Baoding 071000, China; 4.College of Science, Agricultural University of Hebei, Baoding 071001, China

Received:2016-01-15 Online:2016-07-25 Published:2016-07-25

Abstract

Abstract: A series of 2-aryl-1,3-benzoxathiin-4-ones were synthesized by aromatic aldehyde and thiosalicylic acid under microwave irradiation for 5 min.The reaction is fast,simple and has high yield.The structures of the synthesized compounds were characterized by IR,NMR,MS spectra and elemental analysis.Antibacterial(Escherichia coli and Dysentery bacillus)activities of the compounds against Escherichia coli and Dysentery bacillus were evaluated.The results showed that 2-aryl-1,3-benzoxathiin-4-ones had good antibacterial activity.

Key words: microwave irradiation, 2-aryl-1,3-benzoxathiin-4-ones, antibacterial activity

CLC Number:

O621.3

FENG Junna,PENG Shaohui,CUI Penglei,CHEN Hua,LI Xiaoliu. Microwave assisted synthesis and antibacterial study of 2-aryl-1,3-benzoxathiin-4-ones[J]. Journal of Hebei University (Natural Science Edition), 2016, 36(4): 396-401.

References

[1] CHEN J,JIANG X W,GU J D.Existence of novel phylotypes of nitrite-dependent anaerobic methane-oxidizing bacteria in surface and subsurface sediments of the south china sea[J].Geomicrobiology Journal,2015,32:1-9.
[2] GAI W Y,WANG J W,WANG J,et al.Molecular classification and drug resistance analysis of Escherichia coli isolated from poultry in China[J].International Journal of Clinical and Experimental Medicine,2015,8(1):836-844.
[3] ZHANG C,LI W L,LIU W H,et al.T4-Like phage bp7,a potential antimicrobial agent for controlling drug-resistant Escherichia coli in chickens[J].Applied and Environmental Microbiology,2013,79(18):5559-5565.
[4] 张继瑜,邓旭明,阎继业,等.痢疾杆菌福氏2a及其环丙沙星耐药株gyrA和parC基因耐药性决定区的序列分析[J].中国兽医科技,2003,33(4):20-25. ZHANG J Y,DENG X M,YAN J Y,et al.Sequencing and analysis of gyrA and parC genes and the QRDRs in laboratory-induced ciprofloxacin-resistant mutants of Shigella flexneri 2a[J].Chinese Journal of Veterinary Science Technology,2003,33(4):20-25.
[5] OAE S,NUMATA T.A novel cyclization reaction of o-carboxyhenyl and o-carbamoylphenyl sulfoxides,Formation of benzoxathiane dihydrobenzothiazine and benzoisothiazoline[J].Tetrahedron,1974,30:2641-2646.
[6] SHIMIZU M,SHIMAZAKI T,YOSHIDA T,et al.Synthesis of 1,2-benzisothiazolin-3-ones by ring transformation of 1,3-benzoxathiin-4-one 1-oxides[J].Tetrahedron,2012,68:3932-3936.
[7] NANDI B,KUNDU N G.A general and highly regio and stereoselective method for the synthesis of(E)-2-(2-arylvinyl)-3,1-benzoxathiin-4-ones through palladium-copper catalysis[J].Journal of the Chemical Society,Perkin Transactions 1,2001:1649-1655
[8] YAMANAKA M,SHIMADA S,ANDO W,et al.Synthesis of 2-alkylidene-3,1-benzoxathiin-4-ones by the pummerer type reaction[J].Phosphorus,Sulfur and Silicon and the Related Elements,2015,190:1307-1308.
[9] NASON H K,MOWRY D T.2-methyl-4-keto-1,3-benzothioxane[P].United States:CP 2496741A,1950-2-7.
[10] SENNING A,LAWESSON S O.A-Substituted sulfides.Ⅸ.The formation of the 4-thiaisochroman-1-one system[J].Acta Chemica Scandinavica,1962,16:1175-1182.
[11] SENNING A,LAWESSON S O.Chemistry of a-substituted sulfides.Ⅲ.Synthesis of 3-aryl-4-thiaisochroman-1-ones[J].Arkiv foer Kemi,1961,17:261-264.
[12] 冯俊娜,李晓慧,邵洁,等.二芳基苯并1,3-噻嗪烷-4-酮衍生物的微波促进合成及其HIV逆转录酶抑制活性[J].有机化学,2015,35(6):1370-1374. FENG J N,LI X H,SHAO J,et al.Microwave assisted synthesis and Anti-HIV-RT activity of diaryl benzo[1,3] thiazin-4-ones[J].Chinese Journal of Organic Chemistry,2015,35(6):1370-1374.
[13] KANAGARAJAN V,GOPALAKRISHNAN M.Domino way toward the synthesis of novel 4-(4-morpholinophenyl)-6-aryl-6H-1,3-thiazin-2-amines under focused microwave irradiation catalyzed by heterogeneous NaHSO₄.SiO₂ and their in vitro microbiological evaluation[J].Pharmaceutial Chemistry Journal,2011,45(4):248-256.
[14] SAIKIA P,GOGOI S,BORUAH R C.A facile synthesis of steroidal and nonsteroidal pyrimidines under microwave irradiation[J].Tetrahedron Letters,2015,56:2106-2109.

Microwave assisted synthesis and antibacterial study of 2-aryl-1,3-benzoxathiin-4-ones

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