AgOTf催化合成(E)-3-(2-苯基-4H-色烯-4-亚基)吲哚酮化合物
|
摘要
文章报道了一种以AgOTf催化2-羟基查尔酮和2-吲哚酮合成(E)-3-(2-苯基-4H-色烯-4-亚基)吲哚酮化合物的方法.该方法经历了迈克尔加成和分子内环化脱氢的串联反应,简便、快速、高产率地构筑了黄酮类衍生物.论文研究了催化剂和放大实验对于产率的影响,产物经~1H NMR、~(13)C NMR、高分辨质谱和红外进行了表征.
An efficient synthetic protocol for(E)-3-(2-phenyl-4H-chromen-4-ylidene) indolin-2-one catalyzed by AgOTf had been developed. The cascade approach used 2-hydroxychalcone and oxindole as raw materials, involving Michael addition followed by intramolecular cyclization and dehydrogenation sequence. This cascade approach has the advantages such as operational simplicity, short reaction time and excellent yields. The effects of catalysts and scaled-up experiment on the yields were investigated. The structures of the obtained compounds were characterized by ~1H NMR, ~(13)C NMR, IR and HRMS.
An efficient synthetic protocol for(E)-3-(2-phenyl-4H-chromen-4-ylidene) indolin-2-one catalyzed by AgOTf had been developed. The cascade approach used 2-hydroxychalcone and oxindole as raw materials, involving Michael addition followed by intramolecular cyclization and dehydrogenation sequence. This cascade approach has the advantages such as operational simplicity, short reaction time and excellent yields. The effects of catalysts and scaled-up experiment on the yields were investigated. The structures of the obtained compounds were characterized by ~1H NMR, ~(13)C NMR, IR and HRMS.
引文
[1]杨震.活性天然产物和结构多样性类天然产物的合成[J].化学进展,2009,21(1):47-54.Yang Z.Syntheses of biological active natural products and natural product-like molecule[J].Progress in Chemistry,2009,21(1):47-54.
[2]杜灿屏,陈拥军,梁文平,等.天然产物化学研究的挑战和机遇[J].化学进展,2002,14(5):405-407.DOI:10.3321/j.issn:1005-281X.2002.05.012.Du C P,Chen Y J,Liang W P,et al.The challenge and opportunity of the natural product chem istry[J].Progress in Chemistry,2002,14(5):405-407.
[3]崔时胜,罗大云,林军,等.2-氰基-2-(1,3-二烷基咪唑烷-2-亚基)乙酸乙酯衍生物的合成[J].云南大学学报:自然科学版,2017,39(1):120-123.Cui S S,Luo D Y,Lin J,et al.Synthesis of ethyl 2-cyano-2-(1,3-dialkylimidazolidin-2-ylidene)acetate derivatives[J].Journal of Yunnan University:Natural Sciences Edition,2017,39(1):120-123.
[4]郝晓盼,姜秀阳,林军,等.1,3-二氮杂环并[1,2-c]-1,2,3-三唑的简便合成[J].云南大学学报:自然科学版,2015,37(5):766-769.He X F,Jiang X Y,Lin J,et al.A convenient synthesis of 1,3-diazaheterocycle-fused[1,2-c]-1,2,3-triazoles[J].Journal of Yunnan University:Natural Sciences Edition,2015,37(5):766-769.
[5]罗大云,杨昌龙,资全兴,等.茚并[1,2-b]吡咯-4(1H)-酮类化合物的合成[J].云南大学学报:自然科学版,2018,40(1):125-131.Luo D Y,Yang C L,Zi Q X,et al.Synthesis of indeno[1,2-b]pyrrol-4(1H)-one compounds[J].Journal of Yunnan University:Natural Sciences Edition,2018,40(1):125-131.
[6]范鸣.抗腹泻药Crofelemer[J].药学进展,2011,35(3):138-139.Fan M.Antidiarrheal drugs Crofelemer[J].Progress in Pharmaceutical Sciences,2011,35(3):138-139.
[7]Sagrera G,Bertucci A,Vazquez A,et al.Synthesis and antifungal activities of natural and synthetic biflavonoids[J].Bioorganic&Medicinal Chemistry,2011,19(10):3 060-3 073.
[8]Rahman M,Riaz M,Desai U R.Synthesis of biologically relevant biflavanoids-A review[J].Chemistry&Biodiversity,2007,4(11):2 495-2 527.
[9]Sashidhara K V,Kumar A,Agarwal S,et al.A simple and efficient access to new functionalized 4-phenacylideneflavenes[J].Advanced Synthesis&Catalysis,2012,354(6):1 129-1 140.
[10]Yin G D,Fan L,Ren T,et al.Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction[J].Organic&Biomolecular Chemistry,2012,10(44):8 877-8 883.
[11]Kemnitzer W,Drewe J,Jiang S,et al.Discovery of4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high throughput screening assay.4.Structure-activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions[J].Journal of Medicinal Chemistry,2008,51(3):417-423.DOI:10.1021/jm7010657.
[12]Sepay N,Mallik S,Guha C,et al.An efficient synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene)pyrimidine-2,4,6(1H,3H,5H)-triones and investigation of their interactions withβ-lactoglobiulin[J].RSC Advances,2016,6(98):96 016-96 024.DOI:10 .1039/C6RA13584F.
[13]Yin G D,Lai T T,Yan Z S,et al.Catalyst-free C-S/C-O bond formation:synthesis of novel 4-thiosubstituted 2-aryl-4H-chromenes from easily available 2-hydroxychalcones[J].Tetrahedron,2013,69(11):2 430-2 435.DOI:10.1016/j.tet.2013.01.047.
[14]Guo J M,Wang W B,Guo J,et al.Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel-Crafts alkylation/ketalization sequence[J].RSC Advances,2018,8(28):15 641-15 651.DOI:10.1039/C8RA02481B.
[15]Tang C K,Zhou Z Y,Xia A B,et al.Combining organocatalysis and iodine catalysis:One-pot sequential catalytic synthesis of chiral spirodihydrobenzofuran pyrazolones and spirodihydrobenzofuran oxindoles[J].Organic Letters,2018,20(18):5 840-5 844.DOI:10.1021/acs.orglett.8b02525.
[16]周彦佑,常顺琴,陈爽,等.新型螺环吡咯酮双氧化吲哚类化合物的无催化剂合成及其抗白血病活性[J].合成化学,2018,26(12):914-917.Zhou Y Y,Chang S Q,Chen S,et al.Catalystfree synthesis and anti-human leukemia cells activities of novel dispiropyrrolidinyloxindoles[J].Chinese Journal of Synthetic Chemistry,2018,26(12):914-917.
[17]张和智,欧阳贵平,陈洪,等.2-吲哚酮类化合物的研究进展[J].精细化工中间体,2016,46(1):9-16.Zhang H Z,Ouyang G P,Chen H,et al.Review of oxindole compounds studies[J].Fine Chemical Intermediates,2016,46(1):9-16.
[18]黄朋勉,周智慧,杜永磊,等.N-烷氧基取代酰胺类化合物的合成及杀菌活性[J].有机化学,2018,38:1-10.Huang P M,Zhou Z H,Du Y L,et al.Synthesis and fungicidal activity of N-alkoxyl amide derivatives[J].Chinese Journal of Organic Chemistry,2018,38:1-10.
[19]Guha C,Samanta S,Sepay N,et al.A facile synthesis of 2-(2-phenyl-4H-chromen-4-ylidene)-2H-indene-1,3-diones and related compounds involving an interesting aerial oxidation[J].Tetrahedron Letters,2015,56(34):4 954-4 958.DOI:10.1016/j.tetlet.2015.07.005.
[20]Bakthadoss M,Meegada S K,Surendar M.Triple domino reaction for the synthesis of pyrazole/indoline linked chromenes[J].Tetrahedron,2018,74(4):490-496.DOI:10.1016/j.tet.2017.12.021.
[21]刘冠男,周宇,蒋华良,等.银催化有机合成反应的研究进展[J].化学进展,2011,23(6):1 137-1 147.Liu G N,Zhou Y,Jiang H L,et al.Recent advances in silver-mediated organic synthesis reactions[J].Progress in Chemistry,2011,23(6):1 137-1 147.
[22]王晓晶,杨淬,黄超,等.剑叶龙血素A衍生物的合成及其镇痛活性研究[J].云南大学学报:自然科学版,2018,40(4):748-754.Wang X J,Yang C,Huang C,et al.Synthesis and analgesic activity evaluation of cochinchinenin A derivatives[J].Journal of Yunnan University:Natural Sciences Edition,2018,40(4):748-754.
[2]杜灿屏,陈拥军,梁文平,等.天然产物化学研究的挑战和机遇[J].化学进展,2002,14(5):405-407.DOI:10.3321/j.issn:1005-281X.2002.05.012.Du C P,Chen Y J,Liang W P,et al.The challenge and opportunity of the natural product chem istry[J].Progress in Chemistry,2002,14(5):405-407.
[3]崔时胜,罗大云,林军,等.2-氰基-2-(1,3-二烷基咪唑烷-2-亚基)乙酸乙酯衍生物的合成[J].云南大学学报:自然科学版,2017,39(1):120-123.Cui S S,Luo D Y,Lin J,et al.Synthesis of ethyl 2-cyano-2-(1,3-dialkylimidazolidin-2-ylidene)acetate derivatives[J].Journal of Yunnan University:Natural Sciences Edition,2017,39(1):120-123.
[4]郝晓盼,姜秀阳,林军,等.1,3-二氮杂环并[1,2-c]-1,2,3-三唑的简便合成[J].云南大学学报:自然科学版,2015,37(5):766-769.He X F,Jiang X Y,Lin J,et al.A convenient synthesis of 1,3-diazaheterocycle-fused[1,2-c]-1,2,3-triazoles[J].Journal of Yunnan University:Natural Sciences Edition,2015,37(5):766-769.
[5]罗大云,杨昌龙,资全兴,等.茚并[1,2-b]吡咯-4(1H)-酮类化合物的合成[J].云南大学学报:自然科学版,2018,40(1):125-131.Luo D Y,Yang C L,Zi Q X,et al.Synthesis of indeno[1,2-b]pyrrol-4(1H)-one compounds[J].Journal of Yunnan University:Natural Sciences Edition,2018,40(1):125-131.
[6]范鸣.抗腹泻药Crofelemer[J].药学进展,2011,35(3):138-139.Fan M.Antidiarrheal drugs Crofelemer[J].Progress in Pharmaceutical Sciences,2011,35(3):138-139.
[7]Sagrera G,Bertucci A,Vazquez A,et al.Synthesis and antifungal activities of natural and synthetic biflavonoids[J].Bioorganic&Medicinal Chemistry,2011,19(10):3 060-3 073.
[8]Rahman M,Riaz M,Desai U R.Synthesis of biologically relevant biflavanoids-A review[J].Chemistry&Biodiversity,2007,4(11):2 495-2 527.
[9]Sashidhara K V,Kumar A,Agarwal S,et al.A simple and efficient access to new functionalized 4-phenacylideneflavenes[J].Advanced Synthesis&Catalysis,2012,354(6):1 129-1 140.
[10]Yin G D,Fan L,Ren T,et al.Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction[J].Organic&Biomolecular Chemistry,2012,10(44):8 877-8 883.
[11]Kemnitzer W,Drewe J,Jiang S,et al.Discovery of4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell-and caspase-based high throughput screening assay.4.Structure-activity relationships of N-alkyl substituted pyrrole fused at the 7,8-positions[J].Journal of Medicinal Chemistry,2008,51(3):417-423.DOI:10.1021/jm7010657.
[12]Sepay N,Mallik S,Guha C,et al.An efficient synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene)pyrimidine-2,4,6(1H,3H,5H)-triones and investigation of their interactions withβ-lactoglobiulin[J].RSC Advances,2016,6(98):96 016-96 024.DOI:10 .1039/C6RA13584F.
[13]Yin G D,Lai T T,Yan Z S,et al.Catalyst-free C-S/C-O bond formation:synthesis of novel 4-thiosubstituted 2-aryl-4H-chromenes from easily available 2-hydroxychalcones[J].Tetrahedron,2013,69(11):2 430-2 435.DOI:10.1016/j.tet.2013.01.047.
[14]Guo J M,Wang W B,Guo J,et al.Diastereoselective construction of 4-indole substituted chromans bearing a ketal motif through a three-component Friedel-Crafts alkylation/ketalization sequence[J].RSC Advances,2018,8(28):15 641-15 651.DOI:10.1039/C8RA02481B.
[15]Tang C K,Zhou Z Y,Xia A B,et al.Combining organocatalysis and iodine catalysis:One-pot sequential catalytic synthesis of chiral spirodihydrobenzofuran pyrazolones and spirodihydrobenzofuran oxindoles[J].Organic Letters,2018,20(18):5 840-5 844.DOI:10.1021/acs.orglett.8b02525.
[16]周彦佑,常顺琴,陈爽,等.新型螺环吡咯酮双氧化吲哚类化合物的无催化剂合成及其抗白血病活性[J].合成化学,2018,26(12):914-917.Zhou Y Y,Chang S Q,Chen S,et al.Catalystfree synthesis and anti-human leukemia cells activities of novel dispiropyrrolidinyloxindoles[J].Chinese Journal of Synthetic Chemistry,2018,26(12):914-917.
[17]张和智,欧阳贵平,陈洪,等.2-吲哚酮类化合物的研究进展[J].精细化工中间体,2016,46(1):9-16.Zhang H Z,Ouyang G P,Chen H,et al.Review of oxindole compounds studies[J].Fine Chemical Intermediates,2016,46(1):9-16.
[18]黄朋勉,周智慧,杜永磊,等.N-烷氧基取代酰胺类化合物的合成及杀菌活性[J].有机化学,2018,38:1-10.Huang P M,Zhou Z H,Du Y L,et al.Synthesis and fungicidal activity of N-alkoxyl amide derivatives[J].Chinese Journal of Organic Chemistry,2018,38:1-10.
[19]Guha C,Samanta S,Sepay N,et al.A facile synthesis of 2-(2-phenyl-4H-chromen-4-ylidene)-2H-indene-1,3-diones and related compounds involving an interesting aerial oxidation[J].Tetrahedron Letters,2015,56(34):4 954-4 958.DOI:10.1016/j.tetlet.2015.07.005.
[20]Bakthadoss M,Meegada S K,Surendar M.Triple domino reaction for the synthesis of pyrazole/indoline linked chromenes[J].Tetrahedron,2018,74(4):490-496.DOI:10.1016/j.tet.2017.12.021.
[21]刘冠男,周宇,蒋华良,等.银催化有机合成反应的研究进展[J].化学进展,2011,23(6):1 137-1 147.Liu G N,Zhou Y,Jiang H L,et al.Recent advances in silver-mediated organic synthesis reactions[J].Progress in Chemistry,2011,23(6):1 137-1 147.
[22]王晓晶,杨淬,黄超,等.剑叶龙血素A衍生物的合成及其镇痛活性研究[J].云南大学学报:自然科学版,2018,40(4):748-754.Wang X J,Yang C,Huang C,et al.Synthesis and analgesic activity evaluation of cochinchinenin A derivatives[J].Journal of Yunnan University:Natural Sciences Edition,2018,40(4):748-754.
© 2004-2018 中国地质图书馆版权所有 京ICP备05064691号 京公网安备11010802017129号 地址：北京市海淀区学院路29号 邮编：100083 电话：办公室：(+86 10)66554848；文献借阅、咨询服务、科技查新：66554700 |