2-芳基苯并［1,3］噁噻烷-4-酮衍生物的微波促进合成及抗菌活性

doi:10.3969/j.issn.1000-1565.2016.04.011

河北大学学报(自然科学版) ›› 2016, Vol. 36 ›› Issue (4): 396-401.DOI: 10.3969/j.issn.1000-1565.2016.04.011

2-芳基苯并［1,3］噁噻烷-4-酮衍生物的微波促进合成及抗菌活性

冯俊娜^1,2,彭绍辉³,崔朋雷^1,4,陈华¹,李小六¹

收稿日期:2016-01-15 出版日期:2016-07-25 发布日期:2016-07-25
通讯作者: 陈华(1977—),男,江西贵溪人,河北大学教授,博士,主要从事有机合成方面的研究.E-mail:hua-todd@163.com
作者简介:冯俊娜(1982—),女,河北保定人,中国地质大学长城学院讲师,主要从事有机合成方面的研究. E-mail:794497930@qq.com
基金资助:
国家自然科学基金资助项目(21372060);河北省自然科学杰出青年基金(培育)(B2015201005);河北省高等学校科学技术项目(Z2015157);保定市科技局项目(15ZF072);中国地质大学长城学院科研项目(ZDCYK01507)

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

摘要/Abstract

摘要： 以芳醛和硫代水杨酸为原料,微波辐射5分钟,合成了2-芳基苯并［1,3］噁噻烷-4-酮衍生物,该反应具有时间短、操作简便、收率高等优点.目标化合物通过IR、NMR、MS和元素分析等方法确定结构.初步测试了化合物对大肠杆菌和痢疾杆菌的抑制活性.结果表明:2-芳基苯并［1,3］噁噻烷-4-酮衍生物有明显地抑菌作用.

关键词: 微波辐射, 2-芳基苯并［1, 3］噁噻烷-4-酮, 抗菌活性

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

中图分类号:

O621.3

冯俊娜,彭绍辉,崔朋雷,陈华,李小六. 2-芳基苯并［1,3］噁噻烷-4-酮衍生物的微波促进合成及抗菌活性[J]. 河北大学学报(自然科学版), 2016, 36(4): 396-401.

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.

参考文献

[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.

2-芳基苯并［1,3］噁噻烷-4-酮衍生物的微波促进合成及抗菌活性

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

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 10

编辑推荐

Metrics

本文评价

[1]	王海强,安向向,侯淑芬,郝盼龙,张秀敏. 39株内生放线菌次级代谢产物的合成潜能[J]. 河北大学学报(自然科学版), 2017, 37(3): 254-261.
[2]	彭绍辉,杜忠文,冯俊娜,董玉环,陈华. 微波辐射合成苹果酸丁酯[J]. 河北大学学报(自然科学版), 2013, 33(5): 502-507.
[3]	李红亚,李术娜,王树香,赵齐齐,朱宝成. (E)-3-芳亚甲基色满酮类化合物的快速合成及其抑真菌活性[J]. 河北大学学报(自然科学版), 2013, 33(4): 380-386.
[4]	翟永清,王莉莉,陈娟,殷天亮,李蕊. 微波辐射法快速合成Eu3+激活的SrMoO4红色荧光粉[J]. 河北大学学报(自然科学版), 2012, 32(6): 602-607.
[5]	李记太,张冬暖,刘卉闵,宋亚丽. 微波辐射一锅法合成N-(4-芳基噻唑-2-基)-腙类化合物[J]. 河北大学学报(自然科学版), 2012, 32(3): 261-264,290.
[6]	李红亚,刘卉闵,吴国江,李术娜,郝庆红,朱宝成. 微波辐射下β-芳氧丙酸和色满酮的合成[J]. 河北大学学报(自然科学版), 2008, 28(4): 399-402.
[7]	边延江,刘会明,吴博,宋艳芳. 微波辐射SnCl4·5H2O催化合成苯甲酸苯乙酯[J]. 河北大学学报(自然科学版), 2005, 25(4): 383-385,404.
[8]	靳通收,冯国良,杨米娜,李同双. 微波辐射下ZrO2/S2O82-催化合成芳香磺酰亚胺[J]. 河北大学学报(自然科学版), 2004, 24(3): 258-262.
[9]	肖立伟,李慧章,刘卉闵,李红亚. 无溶剂微波辐射下的Knoevenagel缩合反应[J]. 河北大学学报(自然科学版), 2003, 23(2): 167-169.
[10]	刘秀英,马志广,郄录江,单金缓,申世刚. 微波辐射无溶剂合成(E)-肉桂酸[J]. 河北大学学报(自然科学版), 2001, 21(4): 440-442.