摘要
总结了文献报道的picarbutrazox的合成工艺路线和具体的合成方法,并对各工艺路线进行了综合评述。Picarbutrazox主要有3条合成工艺路线,是由关键中间体1-甲基-5-苯甲酰基-1H-四唑进行多步反应得到。
The synthetic methods of picarbutrazox reported in the literature were summarized,and a comprehensive reciew of each method was also given. There were three different processes to synthesis picarbutrazox from 1-methyl-5-benzoyltetrazole via multi-step reactions.
引文
[1]叶萱.新颖杀菌剂Picarbutrazox[J].世界农药,2018,40(2):63-64.
[2]HIDEKAZU MIYAZAKI,SATORU YANAKA,et al.Compound containing pyridine ring and method for producing halogenated picoline derivative and tetrazolyloxime derivative:US,20130012713A1[P].2013-01-10.
[3]HIROKI INOUE,KARU NODA.Process for preparation of t-butoxycarbonylamine compounds:US,20130005981[P].2013-01-03.
[4]SUZUKI TATSUMI,SUGIURA TADASHI,et al.Process for preparation of 1-alkyl-5-benzoyl-tetrazole derivatives:EP,2407461A1[P].2009-03-11.
[5]RAAPR.Reactions of 1-substituted 5-tetrazoylliyhium compounds.Preparation of 5-substituted 1-methylterazoles[J].Canadian Journal of Chemistry,1971,49:2139-2142.
[6]CAILLON-MOISSEAU STEPHANE,COQUERON PIERREYVES,et al.Process for the preparation of 5-substituded 1-alkyltetrazoles:WO,2011110651A1[P].2010-03-12.
[7]MIYAZAKI,HIDEKAZU.Manufacture of 1H-tetrazole derivatives by reacting azides with cyanides in flow reactor:WO,2013187327[P].2012-06-12.
[8]ZARAGOZA DOERWALD,FLORENCLO,et al.Method for preparation of certain 1,5-disubstituted tetrazoles:WO,2016142364A1[P].2016-09-15.
[9]PETERYATES,DONALD G.FAUNM.Aliphatic diazo compounds.Ⅷ.The reaction of diazo katones with basesⅡ[J].J.Am.Chem.Soc,1963,85(19):2967-2976.
[10]PLAUNT,ADAM J,HARMATYS KARA M,et al.Library synthesis,screening,and discobery of modified Zinc(Ⅱ)-bis(dipicolylamine)probe for enhanced molecular imaging of cell death[J].Bioconjugate Chemistry,2014,25(4):724-737.
[11]CONWAY JOHN H,FIEDLER DOROTHEA.An affinity reagent for the recognition of pyrophosphorylated peptides[J].Angewandte Chemie,2015,54(13):3941-3945.
[12]ASKEW BENNY C,DEMORIN FRENEL F,et al.Preparation of N-thiazolyl-N′-pyridyl ureas as antitumor agents:US,20020193405A1[P].2002-12-19.
[13]YAN YINFA,ZHOU PING,et al.Preparation of indolylalkylpyridinamines for inhibition ofβ-secretase:WO,2008036196A2[P].2008-03-27.
[14]BEIER CHRIDRIAN,BENTING JUERGEN,et al.Fungicide hydroximoyltetrazole derivatives:WO,2010000841(A1)[P].2010-01-07.
[15]ITO,SHUICHI,et al.Tetrazoyl oximes,their salts,and their use for plant disease control agents:Jpn.Kokai Tokkyo Koho,2010174009[P].2010-08-12.
[16]ITO,SHUICHI,et al.Tetrazoyl oximes,their salts,and their use for plant disease control agents:Jpn.Kokai Tokkyo Koho,2010174008[P].2010-08-12.