共查询到20条相似文献,搜索用时 15 毫秒
1.
Xiaodong Jia Xiangning Chen Congde Huo Fangfang Peng Chang Qing Xicun Wang 《中国化学》2012,30(7):1504-1510
A multicomponent double Mannich reaction of amines, aldehydes and ketones was efficiently catalyzed by molecular iodine, producing a series of 4‐piperidones in a stereoselective way. A variety of amines, aldehydes and ketones were tolerated in this tandem process, including those with labile functinal groups. Further investigation of the reaction between alkyl‐imines and ketones showed that imines from amines and ketones were formed in situ and isomerized to enamine in the presence of molecular iodine to accelerate the corresponding Mannich addition. 相似文献
2.
The anti-selective direct asymmetric Mannich reaction of (hetero) aromatic aldehydes, 4-anisidine and O-protected hydroxyacetones for the synthesis of stereodefined anti-β-amino-α-hydroxycarbonyl compounds was developed. Protease type XIV from Streptomyces griseus (SGP) was used as a biocatalyst in 1,4-dioxane/phosphate buffer under mild reaction conditions. The excellent diastereoselectivities of up to >99:1 (anti/syn) and good enantioselectivities of up to 90% ee were achieved. This method provides a more sustainable complement to chemically catalyzed anti-selective direct asymmetric Mannich reactions. 相似文献
3.
Yinman Chan 《Tetrahedron》2010,66(35):7179-7999
The double Mannich reaction of acyclic α,γ-substituted β-keto esters and bis(aminol) ethers gives substituted 3,5-substituted-4-piperidones with high levels of diastereoselectivity. These piperdiones can be easily transformed into substituted E-ring analogues of the delphinium alkaloid methyllycacotine. 相似文献
4.
Sankaranarayanan Jayashree 《合成通讯》2018,48(14):1805-1815
An efficient one-pot protocol for the synthesis of 2-((substituted amino)(4-phenyl)methyl)-3-hydroxy-naphthalene-1,4-dione derivatives has been developed by the three-component reaction of 2-hydroxy-naphthalene-1,4-dione, aromatic aldehydes and anilines/heterocyclic amines using montmorillonite K-10 as a catalyst. The advantages of this method include short reaction time, excellent yield and easy work-up. 相似文献
5.
2 甲基辛醇和 2 甲基癸醇是合成松树叶蜂Diprionpini性信息素活性组分的关键中间体[1 ] ,可以由相应的 2 甲基辛酸和 2 甲基癸酸还原得到。2 甲基脂肪酸的合成有很多报道 ,Mayers等[2 ] 对手性唑啉阴离子进行烷基化 ,然后酸解 ,得到 2 甲基脂肪酸 ;Bystrom等[3] 以 2 乙基 4 甲氧基 唑啉为起始反应物 ,用碘辛烷对其进行烷基化 ,然后酸解 ,得到 2 甲基癸酸 ,收率 60 %。Evans等[4] 则以N 酰基唑烷酮为起始反应物 ,合成 2 甲基辛酸 ,收率大于 70 %。Hogberg等[5] 对脯氨酸甲酯进行两次烷基化 ,然后酸解 ,得到 2 甲基脂肪酸 … 相似文献
6.
Richard Gil 《Tetrahedron》2004,60(13):3085-3090
Samarium diiodide is a catalyst for the reaction of cyclic and acyclic tert-butyldimethylsilyl enoxysilanes with chelating imines. Reaction products are isolated as β-aminoenoxysilanes instead of β-aminoketones as previously observed with the corresponding trimethylsilyl enoxysilanes. Several mechanistic pathways are discussed. 相似文献
7.
Renming Pan Jiaxing Zhang Changwu Zheng Hongyu Wang Dongdong Cao Weiguo Cao Gang Zhao 《Tetrahedron》2017,73(17):2349-2358
Quaternary phosphonium ion-pair or a salt derived from amino acid has been developed to catalyze the Mannich-type reaction of α-substituted ethyl cyanoacetates and 2-(2-nitrophenyl) acetonitrile to N-Boc imines. Experiments shown that more active cyanoacetates could be catalyzed by the gentle phosphonium ion-pair catalysis, while 2-(2-nitrophenyl) acetonitrile as the substrate has to be activated by quaternary phosphonium salts and strong base. All the reactions gave the corresponding highly functionalized chiral β-amino nitriles products with good yields, high diastereo- and enantioselectivities in mild conditions. 相似文献
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《Tetrahedron letters》2014,55(52):7177-7180
The tricyclic core skeleton of lycopodine was constructed by the intramolecular Mannich reaction of a 12-membered cyclic amine. The concise assembly of the macrocyclic intermediate was executed by the sequential inter- and intramolecular N-alkylation of a linear diol using Ns-amide. The fully functionalized diol was prepared via Michael reaction of enone and malonate. The key Mannich reaction proceeded smoothly in the presence of silica gel to provide the tricyclic core skeleton of lycopodine. 相似文献
11.
Mariusz Urbaniak 《Tetrahedron》2006,62(7):1508-1511
The conditions of a simple synthesis of tetra(alkoxymethyl) derivatives of resorcinarene via the Mannich reaction catalysed with iminodiacetic acid are described. A possibility of high yield synthesis of such derivatives for the selected straight-chain alcohols is shown. A possible mechanism of this reaction is suggested. 相似文献
12.
Nada Jaber 《Tetrahedron》2004,60(13):3075-3083
Samarium diiodide, as well as lanthanide triiodides catalyze a one-pot procedure allowing to perform sequentially the Mukaiyama-Michael addition of a ketene silyl acetal on a cyclic α,β-unsaturated ketone, followed by the addition of a glyoxylic, aromatic or heteroaromatic imine. According to the nature of the silyl group the adducts resulting from this tandem process are isolated as ketones or as enoxysilanes. The presence of a coordinating group on the imine increases the rate of the reaction. 相似文献
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14.
Osamu Morikawa 《Tetrahedron letters》2007,48(42):7489-7492
Mannich reaction of resorcin[4]arene with N,N′-diethylethylenediamine and formaldehyde produced a singly bridged resorcinarene-dimer bearing sixteen hydroxyl groups at their peripheral positions, which exists in a closed capsular conformation including the diazahexamethylene bridge chain between the two resorcinarene units in CD3OD. 相似文献
15.
Lluvia Itzel López-López Sendar Daniel Nery-Flores Aidé Sáenz-Galindo Denisse de Loera 《合成通讯》2017,47(23):2247-2253
Mannich bases are formed in a noncatalytic multicomponent reaction, which is promoted by ultrasound irradiation. The procedure avoids the use of toxic solvents, catalyst, and purification, generating the desired compounds in excellent yields and short reaction times. 相似文献
16.
对-甲苯乙酮与芳香醛和芳香胺的Mannich反应 总被引:6,自引:0,他引:6
Mannich反应是合成新化合物的重要方法 [1] ,其对应的产物 Mannich碱常常具有广泛的生物活性 [2 ] .文献报道 ,对 -甲苯乙酮的 Mannich碱具有抑癌 [3]和麻醉拮抗 [4 ]等生物活性 ,但是文献中对 -甲苯乙酮 Mannich碱的合成却是从胺交换法 [5] 、酮交换法 [6] 、查耳酮与胺的 Michael加成[7] 、Schiff碱与酮的缩合 [8~ 14 ] 、β-内酰胺与有机锂的亲核裂解 [15] 等间接方法得到的 .即使是从直接法合成 ,一般也是甲醛参与的 Mannich反应 .虽然芳香醛和芳香胺同时参与的 Mannich反应已有报道 [16] ,但对 -甲苯乙酮与芳香醛和芳香胺直接进行… 相似文献
17.
V. S. Kochubey Ya. S. Blochin O. G. Rodin V. P. Perevalov 《Chemistry of Heterocyclic Compounds》2006,42(7):897-900
An aza-Wittig reaction has been used for the first time in the synthesis of substituted 2-amino-5,6-dihydropyrimidin-4-ones
via condensation of triphenyliminophosphoranes with aromatic heterocumulenes (arylisocyanates and thiocyanates).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1037–1041, July, 2006. 相似文献
18.
The first direct asymmetric Mannich reaction of malononitrile to N‐Boc‐protected imines has been developed with cinchona alkaloid as catalyst. The procedure could tolerate a relatively wide range of substrates, and results in excellent yields and good enantioselectivities even in the presence of only 1 mol% of catalyst loading. The present work provides an easy access to β‐amino malononitrile derivatives. 相似文献
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An efficient and practical procedure for the Mannich reaction of secondary amine, formaldehyde, and indole or N‐methylindole employing zinc chloride is presented. A series of gramine derivatives were obtained in 58–98% yields at room temperature in EtOH by using this method. 相似文献