N,N-二甲氨酰基三甲基硅烷与一系列α-羰基酰胺在无水无氧、105℃的条件下反应,较高产率地合成了α-羟基-α-氨甲酰基酰胺类化合物或α-三甲基硅氧基-α-氨甲酰基酰胺衍生物.其结构用元素分析、1H NMR、13C NMR和IR等技术手段进行了表征.通过研究反应机理和影响反应的因素发现,在α-羰基上连的烃基的空间位阻是该加成反应的重要影响因素,而电子效应则影响反应的速率.提出了可能的反应机理.
参考文献
[1] | Jianxin Chen;Robert F. Cunico.#alpha#-(Dimethylamino)amides from a carbamoylsilane and iminium salts[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,200247(47):8595-8597. |
[2] | Jianxin Chen;Robert F. Cunico.α-Aminoamides from a carbamoylsilane and aldehyde imines[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,200343(43):8025-8027. |
[3] | Chen JX;Pandey RK;Cunico RF.Diastereoselective formation of alpha-aminoamides from carbamoylsilanes and aldehyde imines[J].Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry,20055(5):941-947. |
[4] | 郭文彦;陈建新.α-氨基酰胺类化合物的合成新方法[J].应用化学,2013(10):1114-1119. |
[5] | Jianxin Chen;Robert F. Cunico.Synthesis of α-Ketoamides from a Carbamoylsilane and Acid Chlorides[J].The Journal of Organic Chemistry,200416(16):5509-5511. |
[6] | Robert F. Cunico;Bikash C. Maity.Direct Carbamoylation of Aryl Halides[J].Organic letters,200224(24):4357-4359. |
[7] | Robert F. Cunico;Bikash C. Maity.Direct Carbamoylation of Alkenyl Halides[J].Organic letters,200326(26):4947-4949. |
[8] | Robert F. Cunico;Rajesh K. Pandey.Palladium-Catalyzed Synthesis of α-Iminoamides from Imidoyl Chlorides and a Carbamoylsilane[J].The Journal of Organic Chemistry,200513(13):5344-5346. |
[9] | Robert F.Cunic;Rajesh K.Pandey.Palladium-Catalyzed Conversion of Benzylic and Allylic Halides into alpha-Aryl and beta,gamma-Unsaturated Tertiary Amides by the Use of a Carbamoylsilane[J].The Journal of Organic Chemistry,200522(22):9048-9050. |
[10] | Robert F. Cunico.α-Siloxyamides from a carbamoylsilane and carbonyl compounds[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,20023(3):355-358. |
[11] | Omar Merino;Blanca M. Santoyo;Luisa E. Montiel.Versatile synthesis of quaternary 1,3-oxazolidine-2,4-diones and their use in the preparation of α-hydroxyamides[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,201029(29):3738-3742. |
[12] | Shteinberg L Y.Catalysis of the Reaction of 4-Nitrobenzoic Acid with Ammonia[J].Russian Journal of Applied Chemistry,200982(4):619-623. |
[13] | Kuduk SD;Chang RK;Dipardo RM;Di-Marco CN;Murphy KL;Ransom RW;Reiss DR;Tang C;Prueksaritanont T;Pettibone DJ;Bock MG.Bradykinin B1 receptor antagonists: an alpha-hydroxy amide with an improved metabolism profile.[J].Bioorganic and Medicinal Chemistry Letters,200818(18):5107-5110. |
[14] | Schollkopf U;Beckhaus H.α-Hydroxycarboxamides from N,N-Bis (methoxymethyl) carbamoyllithium[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,197615:293. |
[15] | Ramon D J;Yus M.Carbamoyl and Thiocarbamoyllithium:A New Route by Naphthalene-catalysed Chlorine-lithium Exchange[J].Tetrahedron Letters,199334(39):7115-7118. |
[16] | Nudelman NS.;Linares GEG..New insights into the chemistry of lithium carbamoyls: Characterization of an adduct (R2NC(O)CLi(OLi)NR2)[J].The Journal of Organic Chemistry,20006(6):1629-1635. |
[17] | Banff L;Riva R.Passerini Reaction[J].organic reaction,200565:1-135. |
[18] | Domling A.;Ugi I..Multicomponent reactions with isocyanides [Review][J].Angewandte Chemie International Edition,200018(18):3169-3210. |
[19] | Yue T;Wang M X;Wang D X.Brented Acid Catalyzed Enantioselective Three-component Reaction Involving the α-Addition of Isocyanides to Imines[J].ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,200948:6717-6721. |
[20] | Tao Yue;Mei-Xiang Wang;De-Xian Wang;Geraldine Masson;Jieping Zhu.Catalytic Asymmetric Passerini-Type Reaction:Chiral Aluminum-Organophosphate-CatalyzedEnantioselective a-Addition of Isocyanides toAldehydes[J].The Journal of Organic Chemistry,200921(21):8396-8399. |
[21] | Robert F. Cunico;Jianxin Chen.On the Preparation of Carbamoylsilanes[J].Synthetic Communications,200311(11):1963-1968. |
[22] | Robert F.Cunico;Adalie Rodriguez Motta.Addition of Carbamoylsilanes to Electrophilically Substituted Alkenes.Preparation of beta-Functionalized Tertiary Amides[J].Organic letters,20055(5):771-774. |
[23] | Robert F.Cunico.Aminooxycarbene behavior of a carbamoylsilane[J].Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry,200116(16):2931-2932. |
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