苯并氮杂环类化合物的绿色合成研究进展
|
摘要
苯并氮杂环化合物以其特殊的结构特点和广泛的生理及药理活性而备受关注,也是医药、化学品及功能化材料的基本原料或关键中间体,因此其绿色合成方法的研究是有机化学及药学领域的研究热点之一.苯并五元、六元、七元氮杂环化合物通常是由邻氨基苯酚(硫酚、二胺)与不同结构的羰基化合物反应制得,本文中,笔者阐述了近年来苯并五元、六元、七元氮杂环化合物的绿色合成方法的研究进展,归纳、整理、总结各类反应的特点和优势,并展望了其合成及应用的前景.
Benzazepines have attracted much attention due to their special structural characteristics and extensive physiological and pharmacological activities.They are also the basic raw materials or key intermediates for pharmaceuticals,chemicals and functional materials.Therefore,the research on its green synthesis method is one of the research hotspots in the field of organic chemistry and pharmacy.And this paper elaborated the process of successfully synthesizing various 5-,6-and 7-benzazepines by nucleophilic reactions of o-aminobenzenephenol(thiol,diami) with carbonyl compounds,promoting the development of the modern green synthesis method of benzazepines.The application prospect on green synthesis of benzazepines is also discussed.
Benzazepines have attracted much attention due to their special structural characteristics and extensive physiological and pharmacological activities.They are also the basic raw materials or key intermediates for pharmaceuticals,chemicals and functional materials.Therefore,the research on its green synthesis method is one of the research hotspots in the field of organic chemistry and pharmacy.And this paper elaborated the process of successfully synthesizing various 5-,6-and 7-benzazepines by nucleophilic reactions of o-aminobenzenephenol(thiol,diami) with carbonyl compounds,promoting the development of the modern green synthesis method of benzazepines.The application prospect on green synthesis of benzazepines is also discussed.
引文
[1] OLAH G,PRAKASH G,VAGHOO H,et al.NafionR-H Catalyzed Synthesis of Fluorinated Benzimidazolines,Benzothia-zolines,Benzoxazolines and Dihydrobenz-oxazinones[J].Synthesis,2008,6:897-902.doi:10.1055/s-2008-1032182
[2] SHIVAJI N,THORE D V,DEKHANE S S,et al.Synthesis of Benzimidazolones,Benzooxazolones,2-aminobenzothiazolea from Ethyl Cyanoformate and Ophenylene Diamines,Oaminophenols,Oaminothiophenols Promoted by Lithium Bro-mide[J].Lett Org Chem,2011,8:406-411.
[3] CHIKHALE R V,PANT A M,MENGHANI S S,et al.Facile and Efficient Synthesis of Benzoxazole Derivatives Using N-ovel Catalytic Activity of PEG-SO3H[J].Arab J Chem,2014,10(6):715-725.doi:10.1016/j.arabjc.2014.06.011
[4] DHAMELIYA T M,CHOURASIYA S S,MISHRA E,et al.Rationalization of Benzazole-2-carboxylate Versus Benzazine-3-one/benzazine-2,3-dione Selectivity Switch During Cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in Aqueous Medium[J].J Org Chem,2017,82:10077-10091.doi:10.1021/acs.joc.7b01548
[5] MAYO M S,YU X,ZHOU X,et al.Convenient Synthesis of Benzothiazoles and Benzimidazoles Through Brnsted Acid Catalyzed Cyclization of 2-amino Thiophenols/anilines with β-diketones[J].Org Lett,2014,16:764-767.doi:10.1021/Ol403475v
[6] SHARMA P,GUPTA M,KANT R,et al.Formation of a Nanorod Shaped Ionogel and Its High Catalytic Activity for One-pot Synthesis of Benzothiazoles[J].New J Chem,2015,39:5116-5120.doi:10.1039/c5nj00454c
[7] SHI X,GUO J,LIU J P,et al.Unexpectedly Simple Synthesis of Benzazoles by Tbuona Catalyzed Direct Aerobic O-xidative Cyclocondensation of O-thio/Hy-droxy/aminoanilines with Alcohols Under Air[J].Chem Eur J,2015,21:9988-9993.doi:10.1002/chem.201501184
[8] MALI J K,MALI D A,TELVEKAR V N,et al.Copper-Ⅱ Mediated Tandem Reaction Between Arom-atic Ketones and 2-aminobenzenethiol for the Synthesis of 2-aroylbenzothiazoles[J].Tetrahedron Lett,2016,57(4):2324-2326.doi:10.1016/j.tetlet.2016.04.058
[9] ZHANG C,CHANG S,QIU L H,et al.Chemodivergent Synthesis of Multisubstit-uted/F-used Pyrroles via Copper-catalyzed Carbene Cascade Reaction of Propargyl Aimin Odiazoacetates[J].Chem Commun(Camb),2016,52:12470-12473.doi:10.1039/c6cc06864b
[10] YU W F,ZHOU Z M,ZHU H B,et al.Synthesis of Telmisartan and Its Derivatives and Evaluation of Their Biological Activities[J].Chin J Org Chem,2006,26:318-323.
[11] CHINNAPPADU B,CHANDRA S,SHIRISH P V,et al.Synthesis and Evaluation of 2-substituted Benzimidazoles[J].World Journal of Pharmacy and Pharmaceutical Sciences,2014,3(10):1538-1549.
[12] BAJAJ S D,MAHODAYA O A,TEKADE P V.A Green,Microwave Assisted and Efficient Protocol for Synthesis of 2-(4-subsitituted Phenyl)-1H-benzimidazole Catalyzed by Nickel Nitrate and Their Molecular Docking Study[J].Heterocyclic Lett,2016,6(4):805-815.
[13] YAVARI I,SOURI S,SIROUSPOUR M,et al.Vinylphosphonium Salt Mediated Reaction Between Alkyl Propiolates and Aminophenols or Hydroxyphenols[J].Synthesis,2006,19:3243-3249.doi:10.1055/S-2006-950230
[14] ANGUIANO J,GARNER T P,MAHALINGAM M.Chemical Modulation of Chaperone-mediated Autophagy by Novel Reti-noic Acid Derivatives[J].Nat Chem Biol,2013,9:374-382.doi:10.1038/Nchembio.1230
[15] EZEOKONKWO M A,UGWUONA F O,UGWU I C,et al.Synthesis and Antibacterial Studies of Some Alkynylated Benzo[A]phenoxazin-5-one and 1,4-naphthoquinone Derivaties[J].Asian J Chem,2015,27:3843-3850.doi:10.14233/ajchem.2015.19012
[16] LI J X,QING H F,JIAN L X,et al.Metal-free Tandem Cyclization/hydrosilylation to Construct Tetrahydroquinoxalines[J].Green Chem,2013,100:1-3.doi:10.1039/C7GC03095A
[17] FLAVIANO M,DOMENICO A,GIUSEPPE T,et al.Synthesis and Antimicrobial Activity of Some Pyrrolo[1,2,3-de]-1,4-benzothiazines[J].Arch Pharm Pharm Med Chem,1998,331:54-58.
[18] STEFANO S,ARNALDO F,GLENN W,et al.From Phenothiazine to 3-phenyl-1,4-benzothiazine Derivatives as Inhibitorsof the Staphylococcus Aureus Nora Multidrug Efflux Pump[J].J Med Chem,2008,51:4321-4330.doi:10.1021/Jm701623q
[19] LIAO Y F,JIANG P C,CHEN S,et al.Synthesis of Phenothiazines from Cyclohexanones and 2-aminobenzenethiols Under Transition-metal-free Conditions[J].RSC Adv,2013,3(40):18605-18608.doi:10.1039/C3ra43989e
[20] LIN Y M,LU G P,WANGR K,et al.Radical Route to 1,4-benzothiazine Derivatives from 2-aminobenzenethiols and Ketones Under Transition-metal-free Conditions[J].Org Lett,2016,18:6424-6427.doi:10.1021/acs.orglett.6b03324
[21] MASHEVSKAYA I V,MOKRUSHIN I G,BOZDYREVA K S,et al.Five Membered 2,3-dioxoheterocycles:Synthesis and Thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones[J].Russ J Org Chem,2011,47:253-257.doi:10.1134/S1070428011020151
[22] LI X Q,ZHOU C,HU Z Y,et al.An Iodobenzenen-catalysed Domino Route Towar-D Quinoxaline Derivatives from Simple Ketone and O-phenylenediamines in One Pot[J].J Chem Res,2013,37(9):579-581.doi:10.3184/174751913X13758803237636
[23] CHADAR D,RAO S S,GEJJI S P,et al.Regioselective Synthesis of a Vitamin K3 Based Dihydrobenzophenazine Derivative:Its Novel Crystal Structure and DFT Studies[J].RSC Adv,2015,5:76419-76423.doi:10.1039/c5ra13169c
[24] CUI X L,SHEN J H,CHENG G L.Method for Preparing Polysubstituted Quino-xaline Derivatives:China,105693632[P/OL].2018-04-17.https://worldwide.espacenet.com/publicationDetails/originalDocument?FT=D&date=20180417&DB=&locale=en_EP&CC=CN&NR=105693632B&KC=B&ND=8
[25] JANICE M,KLUNDER K D,HARGRAVE M W,et al.Novel Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase 2:Tricyclic Pyridobenzoxazepinones and Dibenzoxazepinones[J].J Med Chem,1992,35:1887-1897.doi:10.1021/jm00088a027
[26] GHANDI M,MOMENI T,NAZERI M T,et al.One-pot Three-component Reaction Providing Tricyclic 1,4-benzoxazepine Derivatives[J].Tetrahedron Lett,2013,54(3):2983-2985.doi:10.1016/j.tetlet.2013.03.131
[27] BABAZADED M,HOSSEINZADEH K R,ZAKHIREH S.Eco-friendly Synthesis of Benzoxazepine and Malonamide Derivatives in Aqueous Media[J].Appl Organometal Chem,2016,30:514-518.doi:10.1002/aoc.3463
[28] ANSHU D,MEHA S,KAPIL A,et al.Facile One Pot Microwave Induced Solvent-free Synthesis and Antifungal,Antitu-Bercular Screening of Spiro[1,5]-benzot-hiazepin-2,39[39H]indol-2[19H]-ones[J].Chem Pharm Bull,2003,51(10):1137-1141.doi:10.1248/cpb.51.1137
[29] KAPIL A,ANSHU D.The Expedient Synthesis of 1,5-benzothiazepines as a Family of Cytotoxic Drugs[J].Bioorg Med Chem Lett,2008,18:114-119.doi:10.1016/j.bmcl.2007.11.002
[30] YAN Y,YANG X,WU L.Facile Synthesis of 1,5-benzothiazepines in Water Using Tetrabutylammonium Tribromide[J].Phosphorus,Sulfur and Silicon and the Related Elements,2012,187:573-579.doi:10.1080/10426507.2011.627900
[31] PENG Z,DEYONG Y,YONG C,et al.An Efficient One-pot Procedure for the Synthesis of 1,5-benzothiazepinones Catalyzed by Tetrabutylammonium Fluoride (TBAF)[J].Tetrahedron Lett,2016,57(7):573743-573745.doi:10.1016/j.tetlet.2016.07.012
[32] KUMAR R,CHAUDHARY P,NIMESH S,et al.An Efficient Synthesis of 1,5-benzadiazepine Derivatives Catalyzed by Silver Nitrate[J].Green Chem,2006,8(6):519-521.doi:10.1039/b601993e
[33] FENG S E,XU F,SHEN Q.An Efficient Synthesis of 1,5-benzodiazepine Derivatives by Lanthanide Trichloride-catalyzed Condensation of O-phenylenediamine with A,B-unsaturated Ketone Under Mild Conditions[J].Chinese J Chem,2008,26(7):1163-1167.doi:10.1002/Cjoc.200890213
[34] MURAI K,NAKATANI R,KITA Y,et al.One-pot Three-component Reaction Providing 1,5-benzodiazepine Derivatives[J].Tetrahedron,2008,64(9):11034-11040.doi:10.1016/j.tet.2008.09.076
[35] WANG S L,CHENG C,WU F Y,et al.Microwave-assisted Multi-component Reaction in Water Leading Highly Regioselective Formation of Benzo[f]azulen-1-ones[J].Tetrahedron,2011,67(5):4485-4493.doi:10.1016/j.tet.2011.05.002
[36] MARIAM A A S.A Novel Method for the Syhthesis of Nicotinonitrile and Diazepine Derivatives Under Microwave Irradiation[J].J Saudi Chem Soc,2011,15(2):155-159.doi:10.1016/j.jscs.2010.07.002
[2] SHIVAJI N,THORE D V,DEKHANE S S,et al.Synthesis of Benzimidazolones,Benzooxazolones,2-aminobenzothiazolea from Ethyl Cyanoformate and Ophenylene Diamines,Oaminophenols,Oaminothiophenols Promoted by Lithium Bro-mide[J].Lett Org Chem,2011,8:406-411.
[3] CHIKHALE R V,PANT A M,MENGHANI S S,et al.Facile and Efficient Synthesis of Benzoxazole Derivatives Using N-ovel Catalytic Activity of PEG-SO3H[J].Arab J Chem,2014,10(6):715-725.doi:10.1016/j.arabjc.2014.06.011
[4] DHAMELIYA T M,CHOURASIYA S S,MISHRA E,et al.Rationalization of Benzazole-2-carboxylate Versus Benzazine-3-one/benzazine-2,3-dione Selectivity Switch During Cyclocondensation of 2-aminothiophenols/phenols/anilines with 1,2-biselectrophiles in Aqueous Medium[J].J Org Chem,2017,82:10077-10091.doi:10.1021/acs.joc.7b01548
[5] MAYO M S,YU X,ZHOU X,et al.Convenient Synthesis of Benzothiazoles and Benzimidazoles Through Brnsted Acid Catalyzed Cyclization of 2-amino Thiophenols/anilines with β-diketones[J].Org Lett,2014,16:764-767.doi:10.1021/Ol403475v
[6] SHARMA P,GUPTA M,KANT R,et al.Formation of a Nanorod Shaped Ionogel and Its High Catalytic Activity for One-pot Synthesis of Benzothiazoles[J].New J Chem,2015,39:5116-5120.doi:10.1039/c5nj00454c
[7] SHI X,GUO J,LIU J P,et al.Unexpectedly Simple Synthesis of Benzazoles by Tbuona Catalyzed Direct Aerobic O-xidative Cyclocondensation of O-thio/Hy-droxy/aminoanilines with Alcohols Under Air[J].Chem Eur J,2015,21:9988-9993.doi:10.1002/chem.201501184
[8] MALI J K,MALI D A,TELVEKAR V N,et al.Copper-Ⅱ Mediated Tandem Reaction Between Arom-atic Ketones and 2-aminobenzenethiol for the Synthesis of 2-aroylbenzothiazoles[J].Tetrahedron Lett,2016,57(4):2324-2326.doi:10.1016/j.tetlet.2016.04.058
[9] ZHANG C,CHANG S,QIU L H,et al.Chemodivergent Synthesis of Multisubstit-uted/F-used Pyrroles via Copper-catalyzed Carbene Cascade Reaction of Propargyl Aimin Odiazoacetates[J].Chem Commun(Camb),2016,52:12470-12473.doi:10.1039/c6cc06864b
[10] YU W F,ZHOU Z M,ZHU H B,et al.Synthesis of Telmisartan and Its Derivatives and Evaluation of Their Biological Activities[J].Chin J Org Chem,2006,26:318-323.
[11] CHINNAPPADU B,CHANDRA S,SHIRISH P V,et al.Synthesis and Evaluation of 2-substituted Benzimidazoles[J].World Journal of Pharmacy and Pharmaceutical Sciences,2014,3(10):1538-1549.
[12] BAJAJ S D,MAHODAYA O A,TEKADE P V.A Green,Microwave Assisted and Efficient Protocol for Synthesis of 2-(4-subsitituted Phenyl)-1H-benzimidazole Catalyzed by Nickel Nitrate and Their Molecular Docking Study[J].Heterocyclic Lett,2016,6(4):805-815.
[13] YAVARI I,SOURI S,SIROUSPOUR M,et al.Vinylphosphonium Salt Mediated Reaction Between Alkyl Propiolates and Aminophenols or Hydroxyphenols[J].Synthesis,2006,19:3243-3249.doi:10.1055/S-2006-950230
[14] ANGUIANO J,GARNER T P,MAHALINGAM M.Chemical Modulation of Chaperone-mediated Autophagy by Novel Reti-noic Acid Derivatives[J].Nat Chem Biol,2013,9:374-382.doi:10.1038/Nchembio.1230
[15] EZEOKONKWO M A,UGWUONA F O,UGWU I C,et al.Synthesis and Antibacterial Studies of Some Alkynylated Benzo[A]phenoxazin-5-one and 1,4-naphthoquinone Derivaties[J].Asian J Chem,2015,27:3843-3850.doi:10.14233/ajchem.2015.19012
[16] LI J X,QING H F,JIAN L X,et al.Metal-free Tandem Cyclization/hydrosilylation to Construct Tetrahydroquinoxalines[J].Green Chem,2013,100:1-3.doi:10.1039/C7GC03095A
[17] FLAVIANO M,DOMENICO A,GIUSEPPE T,et al.Synthesis and Antimicrobial Activity of Some Pyrrolo[1,2,3-de]-1,4-benzothiazines[J].Arch Pharm Pharm Med Chem,1998,331:54-58.
[18] STEFANO S,ARNALDO F,GLENN W,et al.From Phenothiazine to 3-phenyl-1,4-benzothiazine Derivatives as Inhibitorsof the Staphylococcus Aureus Nora Multidrug Efflux Pump[J].J Med Chem,2008,51:4321-4330.doi:10.1021/Jm701623q
[19] LIAO Y F,JIANG P C,CHEN S,et al.Synthesis of Phenothiazines from Cyclohexanones and 2-aminobenzenethiols Under Transition-metal-free Conditions[J].RSC Adv,2013,3(40):18605-18608.doi:10.1039/C3ra43989e
[20] LIN Y M,LU G P,WANGR K,et al.Radical Route to 1,4-benzothiazine Derivatives from 2-aminobenzenethiols and Ketones Under Transition-metal-free Conditions[J].Org Lett,2016,18:6424-6427.doi:10.1021/acs.orglett.6b03324
[21] MASHEVSKAYA I V,MOKRUSHIN I G,BOZDYREVA K S,et al.Five Membered 2,3-dioxoheterocycles:Synthesis and Thermolysis of 3-acylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones[J].Russ J Org Chem,2011,47:253-257.doi:10.1134/S1070428011020151
[22] LI X Q,ZHOU C,HU Z Y,et al.An Iodobenzenen-catalysed Domino Route Towar-D Quinoxaline Derivatives from Simple Ketone and O-phenylenediamines in One Pot[J].J Chem Res,2013,37(9):579-581.doi:10.3184/174751913X13758803237636
[23] CHADAR D,RAO S S,GEJJI S P,et al.Regioselective Synthesis of a Vitamin K3 Based Dihydrobenzophenazine Derivative:Its Novel Crystal Structure and DFT Studies[J].RSC Adv,2015,5:76419-76423.doi:10.1039/c5ra13169c
[24] CUI X L,SHEN J H,CHENG G L.Method for Preparing Polysubstituted Quino-xaline Derivatives:China,105693632[P/OL].2018-04-17.https://worldwide.espacenet.com/publicationDetails/originalDocument?FT=D&date=20180417&DB=&locale=en_EP&CC=CN&NR=105693632B&KC=B&ND=8
[25] JANICE M,KLUNDER K D,HARGRAVE M W,et al.Novel Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase 2:Tricyclic Pyridobenzoxazepinones and Dibenzoxazepinones[J].J Med Chem,1992,35:1887-1897.doi:10.1021/jm00088a027
[26] GHANDI M,MOMENI T,NAZERI M T,et al.One-pot Three-component Reaction Providing Tricyclic 1,4-benzoxazepine Derivatives[J].Tetrahedron Lett,2013,54(3):2983-2985.doi:10.1016/j.tetlet.2013.03.131
[27] BABAZADED M,HOSSEINZADEH K R,ZAKHIREH S.Eco-friendly Synthesis of Benzoxazepine and Malonamide Derivatives in Aqueous Media[J].Appl Organometal Chem,2016,30:514-518.doi:10.1002/aoc.3463
[28] ANSHU D,MEHA S,KAPIL A,et al.Facile One Pot Microwave Induced Solvent-free Synthesis and Antifungal,Antitu-Bercular Screening of Spiro[1,5]-benzot-hiazepin-2,39[39H]indol-2[19H]-ones[J].Chem Pharm Bull,2003,51(10):1137-1141.doi:10.1248/cpb.51.1137
[29] KAPIL A,ANSHU D.The Expedient Synthesis of 1,5-benzothiazepines as a Family of Cytotoxic Drugs[J].Bioorg Med Chem Lett,2008,18:114-119.doi:10.1016/j.bmcl.2007.11.002
[30] YAN Y,YANG X,WU L.Facile Synthesis of 1,5-benzothiazepines in Water Using Tetrabutylammonium Tribromide[J].Phosphorus,Sulfur and Silicon and the Related Elements,2012,187:573-579.doi:10.1080/10426507.2011.627900
[31] PENG Z,DEYONG Y,YONG C,et al.An Efficient One-pot Procedure for the Synthesis of 1,5-benzothiazepinones Catalyzed by Tetrabutylammonium Fluoride (TBAF)[J].Tetrahedron Lett,2016,57(7):573743-573745.doi:10.1016/j.tetlet.2016.07.012
[32] KUMAR R,CHAUDHARY P,NIMESH S,et al.An Efficient Synthesis of 1,5-benzadiazepine Derivatives Catalyzed by Silver Nitrate[J].Green Chem,2006,8(6):519-521.doi:10.1039/b601993e
[33] FENG S E,XU F,SHEN Q.An Efficient Synthesis of 1,5-benzodiazepine Derivatives by Lanthanide Trichloride-catalyzed Condensation of O-phenylenediamine with A,B-unsaturated Ketone Under Mild Conditions[J].Chinese J Chem,2008,26(7):1163-1167.doi:10.1002/Cjoc.200890213
[34] MURAI K,NAKATANI R,KITA Y,et al.One-pot Three-component Reaction Providing 1,5-benzodiazepine Derivatives[J].Tetrahedron,2008,64(9):11034-11040.doi:10.1016/j.tet.2008.09.076
[35] WANG S L,CHENG C,WU F Y,et al.Microwave-assisted Multi-component Reaction in Water Leading Highly Regioselective Formation of Benzo[f]azulen-1-ones[J].Tetrahedron,2011,67(5):4485-4493.doi:10.1016/j.tet.2011.05.002
[36] MARIAM A A S.A Novel Method for the Syhthesis of Nicotinonitrile and Diazepine Derivatives Under Microwave Irradiation[J].J Saudi Chem Soc,2011,15(2):155-159.doi:10.1016/j.jscs.2010.07.002