官能化联苯-2-叠氮类化合物的合成
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摘要
本文以1,2-联烯酮与4-叠氮-3-氧代丁酸乙酯为起始原料,经过碳酸钾促进的串联缩合,浓盐酸催化的分子内脱水、异构化,高效地合成了官能化联苯-2-叠氮类化合物,总收率达到81～87%,并经过~1HNMR,~(13)CNMR和HRMS确定了所得化合物的结构。与文献方法相比,该方法还具有起始原料简单、反应条件温和、操作简便等优点。
In this paper,a series of[1,1′-biphenyl]-2-azides were synthesized through cascade condensation of 1,2-allenic ketones with ethyl 4-azido-3-oxobutanoate using K_2CO_3 as promoter followed by its intramolecular dehydration and isomerization under hydrochloric acid catalysis in a total yield of 81～87%.The structures were characterized by ~1HNMR,~(13)CNMR,IR and HRMS.Notable features of this protocol included simple starting materials,mild conditions,and easy to handle.
In this paper,a series of[1,1′-biphenyl]-2-azides were synthesized through cascade condensation of 1,2-allenic ketones with ethyl 4-azido-3-oxobutanoate using K_2CO_3 as promoter followed by its intramolecular dehydration and isomerization under hydrochloric acid catalysis in a total yield of 81～87%.The structures were characterized by ~1HNMR,~(13)CNMR,IR and HRMS.Notable features of this protocol included simple starting materials,mild conditions,and easy to handle.
引文
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[16]Feng T,Tian M,Zhang X,et al.Tunable synthesis of functionalized cyclohexa-1,3-dienes and 2-aminobenzophenones/benzoate from the cascade reactions of allenic ketones/allenoate with amines and enones[J].J Org Chem,2018,83(9):5 313-5 322.
[17]Wang Q,Xu Z,Fan X,Selective synthesis of oxygen-containing heterocycles via tandem reactions of 1,2-allenic ketones with ethyl 4-chloroacetoacetate[J].RSC Adv,2013,3(13):4 156-4 160.
[18]Wang Q,Yang L,Fan X,Selective synthesis of 3-methylene-2,3-dihydrofurans or 1,2,4-trisubstituted furans via tandem reactions of allenic ketones with α-chloro β-keto esters or ketones[J].Synlett,2014,25(5):687-692.
[19]Wang Q,Zhang T,Fan Y,et al.Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions[J].Org Biomol Chem,2018,16(45):8 854-8 858.
[20]张涛,王强.[Bmim]ZnBr3促进的烯胺酯和联烯酮的串联反应合成烟酸酯衍生物[J],有机化学,2018,38(2):498-503.
[21]Wu W,Yao Z,Li Y,et al.Diastereoselective propargylation of α-alkoxy aldehydes with propargyl bromide and zinc.a versatile and efficient method for the synthesis of chiral oxygenated acyclic natural products[J].J Org Chem,1995,60(10):3 257-3 259.
[22]Petasis N A,Teets K A,Enolates of alpha-allenyl ketones:formation and aldol reactions of cumulenolates[J].J Am Chem Soc,1992,114(26):10 328-10 334.
[2]马登学,夏其英.叠氮二氢硼多聚体结构和性质的理论研究[J],化学研究与应用,2001,21(06):852-858.
[3]Brse S,Gil C,Knepper K,et al.Organic azides:an exploding diversity of a unique class of compounds[J].Angew Chem Int Ed,2005,44(33):5 188-5 240.
[4]江玉波,匡春香,韩春美,等.有机叠氮化合物的合成研究进展[J],有机化学,2012,32(12):2 231-2 238.
[5]Takahashi M,Suga D.Synthesis of 2-aryl-3-arylsulfonylindoles and 2-anilino-3-arylsulfonylindoles from 2-(arylsulfonyl)methylanilines using the Aza-Wittig reaction of iminophosphoranes[J].Synthesis,1998,1998(7):986-990.
[6]Barral K,Moorhouse A D,Moses J E.Efficient conversion of aromatic amines into azides:a one-pot synthesis of triazole linkages[J].Org Lett,2007,9(9):1 809-1 811.
[7]Zhu W,Ma D,Synthesis of aryl azides and vinyl azides via proline-promoted CuI-catalyzed coupling reactions[J].Chem Commun,2004,7:888-889.
[8]Tao C,Cui X,Li J,et al.Copper-catalyzed synthesis of aryl azides and 1-aryl-1,2,3-triazoles from boronic acids[J].Tetrahedron Lett,2007,48(20):3 525-3 529.
[9]Goswami M,Bruin B,Metal-catalysed azidation of organic molecules[J].Eur J Org Chem,2017,2017(8):1 152-1 176.
[10]Tang C,Jiao N,Copper-catalyzed C-H azidation of anilines under mild conditions[J].J Am Chem Soc,2012,134(46):18 924-18 927.
[11]Fang H,Dou Y,Ge J,et al.Regioselective and direct azidation of anilines via Cu(II)-catalyzed C-H functionalization in water[J].J Org Chem,2017,82(20):11 212-11 217.
[12]Tsao M L,Gritsan N,James T R,et al.Study of the chemistry of ortho-and para-biphenylnitrenes by laser flash photolysis and time-resolved IR experiments and by B3LYP and CASPT2 calculations[J].J Am Chem Soc,2003,125(31):9 343-9 358.
[13]Ye J,Ma S,Palladium-catalyzed cyclization reactions of allenes in the presence of unsaturated carbon-carbon bonds[J].Acc Chem Res,2014,47(4):989-1 000.
[14]Fan X,He Y,Zhang X,Recent advances in the reactions of 1,2-allenic ketones and α-allenic alcohols[J].Chem Rec,2016,16(3):1 635-1 646.
[15]Shi X,He Y,Zhang Y,et al.Selective syntheses of diversely substituted 2-hydroxy-4′-hydroxybenzophenones through[4+2]or[3+3]annulation of penta-3,4-dien-2-ones with 3-formylchromones[J].Org Chem Front,2017,4(10):1 967-1 971.
[16]Feng T,Tian M,Zhang X,et al.Tunable synthesis of functionalized cyclohexa-1,3-dienes and 2-aminobenzophenones/benzoate from the cascade reactions of allenic ketones/allenoate with amines and enones[J].J Org Chem,2018,83(9):5 313-5 322.
[17]Wang Q,Xu Z,Fan X,Selective synthesis of oxygen-containing heterocycles via tandem reactions of 1,2-allenic ketones with ethyl 4-chloroacetoacetate[J].RSC Adv,2013,3(13):4 156-4 160.
[18]Wang Q,Yang L,Fan X,Selective synthesis of 3-methylene-2,3-dihydrofurans or 1,2,4-trisubstituted furans via tandem reactions of allenic ketones with α-chloro β-keto esters or ketones[J].Synlett,2014,25(5):687-692.
[19]Wang Q,Zhang T,Fan Y,et al.Synthesis of functionalized cyclopentenes through allenic ketone-based multicomponent reactions[J].Org Biomol Chem,2018,16(45):8 854-8 858.
[20]张涛,王强.[Bmim]ZnBr3促进的烯胺酯和联烯酮的串联反应合成烟酸酯衍生物[J],有机化学,2018,38(2):498-503.
[21]Wu W,Yao Z,Li Y,et al.Diastereoselective propargylation of α-alkoxy aldehydes with propargyl bromide and zinc.a versatile and efficient method for the synthesis of chiral oxygenated acyclic natural products[J].J Org Chem,1995,60(10):3 257-3 259.
[22]Petasis N A,Teets K A,Enolates of alpha-allenyl ketones:formation and aldol reactions of cumulenolates[J].J Am Chem Soc,1992,114(26):10 328-10 334.