[HP(HNCH2CH2)3N]NO3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions

Fetterly, Brandon M.; Jana, Nirmal K.; Verkade, John G.

doi:10.1016/j.tet.2005.09.117

Cited by 69 publications

(38 citation statements)

References 92 publications

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“…for C 11 H 13 NO: C,75.40;H,7.48;N,7.99%. 27 5,29.7,97.2,114.1,125.4,139.6,140.5,143.4,198.8;IR (neat) ν max /cm -1 3259w, 3027w, 2918w, 2861w, 1637s, 1571s, 1476m, 1278s, 1171s, 955m, 831m;MS (ES) 190.1232, found: 190.1237Found: C, 75.55;H, 8.04;N, 6.99. Calc.…”

Section: Methodsmentioning

confidence: 99%

“…for C 12 H 15 NO: C, 76.16;H, 7.99; N, 7.40%. 5,96.7,116.7,118.2,134.1,144.7,152.6,198.8;IR (neat) ν max /cm -1 3100br, 3080w, 3032w, 2956w, 2813w, 1635m, 1554m, 1489s, 1263s, 1205s, 830s, 747s 6, 55.7, 96.7, 115.1, 117.9, 134.2, 144.3, 156.3, 198.5; IR (neat) ν max /cm -1 3228w, 3004w, 2956w, 2914w, 2836w, 1634s, 1595m, 1565s, 1477s, 1352m, 1291m, 1201s, 823s 6, 30.0, 61.0, 99.3, 115.2, 125.1, 131.7, 141.7, 144.4, 166.2, 199.8 Hz, 1H); 13 C NMR (151 MHz, CDCl 3 ) δ 29.8, 98.2, 117.4, 128.5, 129.9, 139.3, 142.8, 199.4; IR (neat) ν max /cm -1 3175w, 3093w, 3002w, 2960w, 1643s, 1594s, 1569s, 1472s, 1291s, 1220s, 1090m, 818s 9, 98.3, 115.9, 117.7, 132.8, 139.7, 142.6, 199.4; IR (neat) ν max /cm -1 3177w, 3073w, 2994w, 2908w, 1634m, 1591s, 1566s, 1471s, 1289m, 1180m, 814s, 752s …”

Section: Methodsmentioning

confidence: 99%

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Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring

et al. 2016

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Publisher's copyright statement:This document is the Accepted Manuscript version of a Published Work that appeared in nal form in The Journal of Organic Chemistry, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the nal edited and published work see http://dx.doi.org/10.1021/acs.joc.6b01110. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-pro t purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. AbstractA convenient, mild and effective conjugate addition of 3-butyn-2-one to a variety of anilines in ethanol is reported. The reaction was monitored and characterized through in situ FTIR, and the dynamics of the facile E/Z alkene geometry interconversion of the resultant aniline-derived enaminones was explored through NMR, FTIR and Xray crystallography. A straightforward purification protocol that employs direct Kugelrohr distillation was identified and the method was further extended to other amines and ynones, allowing rapid access to these interesting compounds.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring

et al. 2016

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“…However, successful three component Strecker reactions using ketones and fluorinated ketones are rare (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14). Fluorinated amino acids are becoming increasingly important in pharmaceuticals and other biological applications (15)(16)(17)(18)(19)(20)(21), such as the development of anticancer drugs for the control of tumor growth and drugs for the control of blood pressure and allergies (22).…”

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confidence: 99%

Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs

Prakash

Mathew

Panja

et al. 2007

Proc. Natl. Acad. Sci. U.S.A.

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The synthesis of ␣-aminonitriles and their fluorinated analogs has been carried out in high yield and purity by the Strecker reaction from the corresponding ketones and amines with trimethylsilyl cyanide using gallium triflate in dichloromethane. Monofluoro-, difluro-, or trifluoromethyl groups can be incorporated into the ␣-aminonitrile product by varying the nature of the fluorinated ketones. Study with various fluorinated and nonfluorinated ketones reveals that the choice of proper catalyst and the solvent system (suitable metal triflates as a catalyst and dichloromethane as a solvent) plays the key role in the direct Strecker reactions of ketones.three-component reaction ͉ ␣-aminonitriles

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“…But usually both these additions are carried out in presence of a strong base or acid [8,9]. Several methods are available in the literature by using different catalysts such as Yb(OTf) 3 [10], CeCl 3 ·7H 2 O-NaI [11], InCl 3 [12], Cu(OTf) 2 [13,14], CAN [15], KF/alumina [16,17], LiClO 4 [18], Bi(OTf) 3 [19], Bi(NO) 3 [20], SmI 2 [21], Cu(acac) 2 /ionic liquid [22], ionic liquid/ quaternary ammonium salt [23,24], boric acid [25], borax [26] [30], MnCl 2 [31]etc. Although these methods have their own advantages and quite useful, but some of these methods used a large excess of reagents, hazardous solvents such as acetonitrile or 1,2-dichloroethane, require long time and harsh reaction.…”

Section: Introductionmentioning

confidence: 99%

Conjugated Addition of Amines to Electron Deficient Alkenes: A Green Approach

Mukherjee

Chatterjee

et al. 2017

Chim.Tech.Acta

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A very simple approach has been developed for conjugate addition of a variety of aliphatic and aromatic amines to electron deficient alkenes in presence tea extract at room temperature. General applicability, operational simplicity, aqueous media, mild reaction conditions, environment friendly, high yields and applications of inexpensive and easily available catalyst are the advantages of the present procedure.

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[HP(HNCH2CH2)3N]NO3: an efficient homogeneous and solid-supported promoter for aza and thia-Michael reactions and for Strecker reactions

Cited by 69 publications

References 92 publications

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring

Conjugate Addition of 3-Buytn-2-one to Anilines in Ethanol: Alkene Geometric Insights through In Situ FTIR Monitoring

Gallium (III) triflate catalyzed efficient Strecker reaction of ketones and their fluorinated analogs

Conjugated Addition of Amines to Electron Deficient Alkenes: A Green Approach

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