摘要
以取代苄胺、1-叔丁氧羰基-4-哌啶酮、叠氮基三甲基硅烷(TMSN3)和异腈化合物为原料,经4组分"一锅煮"反应,得到新型四唑并[1,5-a]哌嗪类螺环化合物。研究了温度和溶剂对反应的影响,得到最佳反应条件:以甲醇为溶剂,65℃回流条件下反应48 h。所有产物结构经~1HNMR和MS进行表征。
An efficient one-pot synthesis of spirotetrazole[1,5-a] piperazine-piperidines by the four-component condensation of benzylamine,1-boc-4-piperidinone,TMSN_3 and isocyanides derivatives was reported.The effects of solvent and temperature on the reaction were elucidated and the optimal reaction conditions were obtained.The structures of products were confirmed by ~1HNMR and MS.
引文
[1]KYU Y Y,SUNGEUM Y I.Synthesis of 5-aryl and vinyl tetrazoles by the palladium catalyzed cross coupling reaction[J].Teterhedron Lett.,1995,36(10):1 679-1 682.
[2]姜凤超,王静.微波辐射法合成5-取代四氮唑衍生物[J].精细化工中间体,2006,36(6):22-25.
[3]廖雅萍.1-苯基-5-巯基-1,2,3,4-四氮唑的化学照相特性分析及合成方法的研究[J].影像技术,1999,(2):13-16.
[4]KANG S Y,LEE S H,SEO H J,et al.Tetrazole-biaryl pyrazole derivatives as cannabinoid CB1 receptor antagonists[J].Bioorg.Med.Chem.Lett.,2008,18(7):2 385-2 389.
[5]ALEXANDER J P,CRAVATT B F.The putative endocannabinoid transport blocker LY2183240 is a potent inhibitor of FAAH and several other brain serinehydrolases[J].J.Am.Chem.Soc.,2006,128(30):9 699-9 704.
[6]HULME C,TEMPEST P,MA V,et al.Melanin concentrating hormone receptor antagonistpct:US,2 005 019 167[P].2005-03-03.
[7]LI Jun,WANG Hai-hai,TAO Shi-wei,et al.Discovery of atetrazole-based growth hormonesecretagogue:4-(hydroxybutyl)carbamic acid 2-{5-[1-(2-amino-2-methylpropionylamino)-2-benzyloxyethyl]tetrazol-1-yl}ethyl ester(BMS-317180)[J].J.Med.Chem.,2007,50(24):5 890-5 893.
[8]PATIL P,KHOURY K,HERDTWECKE,et al.MCR synthesis of a tetracyclic tetrazole scaffold[J].Bioorg.Med.Chem.,2015,23(11):2 699-2 715.
[9]张富成,徐积武,贾玉梁,等.叠代化钠下游产品开发现状与应用[J].化工时刊,2010,24(9):44-47.
[10]NIXEY T,KELLY M,HULME C.The one-pot solution phase preparation of fusedtetrazole-ketopiperazines[J].Tetrahedron Lett.,2000,41(45):8 729-8 733.
[11]UMKEHRER M,KOLB J,BURDACK C,et al.Synthesis of tetrazolopiperazine building blocks by a novelmulticomponent reaction[J].Tetrahedron Lett.,2004,45(34):6 421-6 424.
[12]KALINSKI C,UMKEHRER M,GONNARD S,et al.A new and versatile Ugi/SNAr synthesis of fused 4,5-dihydrotetrazolo[1,5-a]quinoxalines[J].Tetrahedron Lett.,2006,47(12):2 041-2 044.