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Journal articles on the topic 'Secondary Amides'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Zarecki, Adam P., Jacek L. Kolanowski, and Wojciech T. Markiewicz. "Microwave-Assisted Catalytic Method for a Green Synthesis of Amides Directly from Amines and Carboxylic Acids." Molecules 25, no. 8 (April 11, 2020): 1761. http://dx.doi.org/10.3390/molecules25081761.

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Amide bonds are among the most interesting and abundant molecules of life and products of the chemical pharmaceutical industry. In this work, we describe a method of the direct synthesis of amides from carboxylic acids and amines under solvent-free conditions using minute quantities of ceric ammonium nitrate (CAN) as a catalyst. The reactions are carried out in an open microwave reactor and allow the corresponding amides to be obtained in a fast and effective manner when compared to other procedures of the direct synthesis of amides from acids and amines reported so far in the literature. The amide product isolation procedure is simple, environmentally friendly, and is performed with no need for chromatographic purification of secondary amides due to high yields. In this report, primary amines were used in most examples. However, the developed procedure seems to be applicable for secondary amines as well. The methodology produces a limited amount of wastes, and a catalyst can be easily separated. This highly efficient, robust, rapid, solvent-free, and additional reagent-free method provides a major advancement in the development of an ideal green protocol for amide bond formation.

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2

Selvakumar, Kumaravel, Kesamreddy Rangareddy, and John F. Harrod. "The titanocene-catalyzed reduction of acetamides to tertiary amines by PhMeSiH2." Canadian Journal of Chemistry 82, no. 8 (August 1, 2004): 1244–48. http://dx.doi.org/10.1139/v04-063.

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A variety of acetamide derivatives are reduced in excellent yields to tertiary amines by PhMeSiH2 in the presence of Cp2TiX2 (X = F or Me) catalysts. The reactions are very clean at 80 °C. At room temperature a secondary reaction, hydrogenolysis of the C(O)N bond, intervenes and reduces the chemoselectivity. Nevertheless, this chemistry provides a simple methodology for the amide/alkylamine transformation using inexpensive, commercially available reagents.Key words: amides, reduction, secondary amides, methylphenylsilane, titanocene, catalysis.

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3

Krieck, Sven, Philipp Schüler, Jan Peschel, and Matthias Westerhausen. "Straightforward One-Pot Syntheses of Silylamides of Magnesium and Calcium via an In Situ Grignard Metalation Method." Synthesis 51, no. 05 (December 13, 2018): 1115–22. http://dx.doi.org/10.1055/s-0037-1610407.

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Calcium bis[bis(trimethylsilyl)amide] (Ca(HMDS)2) is a widely used reagent in diverse stoichiometric and catalytic applications. These processes necessitate a straightforward and large-scale access of this complex. Calcium does not react with primary and secondary amines, but the addition of excess bromoethane to a mixture of calcium turnings and amines in THF at room temperature yields the corresponding calcium bis(amides), calcium bromide and ethane. This in situ Grignard metalation method (iGMM) allows the preparation of calcium bis(amides) from secondary and primary trialkylsilyl-substituted amines and anilines on a multigram scale.1 Background2 The In Situ Grignard Metalation Method (iGMM)3 Properties of [(thf)2M(HMDS)2]4 Applications and Perspective

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4

Zahardis, J., S. Geddes, and G. A. Petrucci. "The ozonolysis of primary aliphatic amines in fine particles." Atmospheric Chemistry and Physics 8, no. 5 (February 29, 2008): 1181–94. http://dx.doi.org/10.5194/acp-8-1181-2008.

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Abstract. The oxidative processing by ozone of the particulate amines octadecylamine (ODA) and hexadecylamine (HDA) is reported. Ozonolysis of these amines resulted in strong NO2– and NO3– ion signals that increased with ozone exposure as monitored by photoelectron resonance capture ionization aerosol mass spectrometry. These products suggest a mechanism of progressive oxidation of the particulate amines to nitroalkanes. Additionally, a strong ion signal at 125 m/z is assigned to the ion NO3– (HNO3). For ozonized mixed particles containing ODA or HDA + oleic acid (OL), with pO3≥3×10–7 atm, imine, secondary amide, and tertiary amide products were measured. These products most likely arise from reactions of amines with aldehydes (for imines) and stabilized Criegee intermediates (SCI) or secondary ozonides (for amides) from the fatty acid. The routes to amides via SCI and/or secondary ozonides were shown to be more important than comparable amide forming reactions between amines and organic acids, using azelaic acid as a test compound. Finally, direct evidence is provided for the formation of a surface barrier in the ODA + OL reaction system that resulted in the retention of OL at high ozone exposures (up to 10−3 atm for 17 s). This effect was not observed in HDA + OL or single component OL particles, suggesting that it may be a species-specific surfactant effect from an in situ generated amide or imine. Implications to tropospheric chemistry, including particle bound amines as sources of oxidized gas phase nitrogen species (e.g.~NO2, NO3), formation of nitrogen enriched HULIS via ozonolysis of amines and source apportionment are discussed.

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5

Zahardis, J., S. Geddes, and G. A. Petrucci. "The ozonolysis of primary aliphatic amines in single and multicomponent fine particles." Atmospheric Chemistry and Physics Discussions 7, no. 5 (October 15, 2007): 14603–38. http://dx.doi.org/10.5194/acpd-7-14603-2007.

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Abstract. The oxidative processing by ozone of the particulate amines octadecylamine (ODA) and hexadecylamine (HDA) is reported. Ozonolysis of these amines resulted in strong NO2− and NO3− ion signals that increased with ozone exposure as monitored by photoelectron resonance capture ionization aerosol mass spectrometry. These products suggest a mechanism of progressive oxidation of the particulate amines to nitro alkanes. Additionally, a strong ion signal at 125 m/z is assigned to the ion NO3−(HNO3). For ozonized mixed particles containing ODA or HDA + oleic acid (OL), with pO3≥3×10−7 atm, imine, secondary amide, and tertiary amide products were measured. These products most likely arise from reactions of amines with aldehydes (for imines) and stabilized Criegee intermediates (SCI) or secondary ozonides (for amides) from the fatty acid. The routes to amides via SCI and/or secondary ozonides was shown to be more important than comparable amide forming reactions between amines and organic acids, using azelaic acid as a test compound. Finally, direct evidence is provided for the formation of a surface barrier in the ODA + OL reaction system that resulted in the retention of OL at high ozone exposures (up to 10−3 atm for 17 s). This effect was not observed in HDA + OL or single component OL particles, suggesting that it may be a species-specific surfactant effect from an in situ generated amide or imine. Implications to tropospheric chemistry, including particle bound amines as sources of oxidized gas phase nitrogen species (e.g. NO2, NO3), formation of nitrogen enriched HULIS via ozonolysis of amines and source apportionment are discussed.

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6

Blondiaux, Enguerrand, and Thibault Cantat. "Efficient metal-free hydrosilylation of tertiary, secondary and primary amides to amines." Chem. Commun. 50, no. 66 (2014): 9349–52. http://dx.doi.org/10.1039/c4cc02894e.

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Hydrosilylation of secondary and tertiary amides to amines is described using catalytic amounts of B(C₆F₅)₃. The organic catalyst enables the reduction of amides with cost-efficient, non-toxic and air stable PMHS and TMDS hydrosilanes. The methodology was successfully extended to the more challenging reduction of primary amides.

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7

Schuhmacher, Anne, Tomoya Shiro, Sarah J. Ryan, and Jeffrey W. Bode. "Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)." Chemical Science 11, no. 29 (2020): 7609–14. http://dx.doi.org/10.1039/d0sc01330g.

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Oxidative amidation of potassium acyltrifluoroborates (KATs) and amines via trifluoroborate iminiums (TIMs) delivers amides without coupling agents. This unusual approach to amides can be applied for the late-stage modification of bioactive molecules and for solid-phase peptide synthesis.

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8

Garg, Jai Anand, Subrata Chakraborty, Yehoshoa Ben-David, and David Milstein. "Unprecedented iron-catalyzed selective hydrogenation of activated amides to amines and alcohols." Chemical Communications 52, no. 30 (2016): 5285–88. http://dx.doi.org/10.1039/c6cc01505k.

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The first example of hydrogenation of activated amides to amines and alcohols catalyzed by an earth-abundant iron metal complex is discovered. A wide range of trifluoromethyl-substituted secondary and tertiary aromatic and aliphatic amides were hydrogenated.

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9

Saha, Sayantani, and Moris S. Eisen. "Mild catalytic deoxygenation of amides promoted by thorium metallocene." Dalton Transactions 49, no. 36 (2020): 12835–41. http://dx.doi.org/10.1039/d0dt02770g.

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The organoactinide-catalyzed (Cp*₂ThMe₂) hydroborated reduction of a wide range of tertiary, secondary, and primary amides to the corresponding amines/amine–borane adducts via deoxygenation of the amides is reported herein.

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10

Yao, Lei, Ming-Yi Wang, Xin-Ke Wang, Yi-Jun Liu, Hang-Fei Chen, Jun Zheng, Wei Nie, et al. "Detection of atmospheric gaseous amines and amides by a high-resolution time-of-flight chemical ionization mass spectrometer with protonated ethanol reagent ions." Atmospheric Chemistry and Physics 16, no. 22 (November 23, 2016): 14527–43. http://dx.doi.org/10.5194/acp-16-14527-2016.

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Abstract. Amines and amides are important atmospheric organic-nitrogen compounds but high time resolution, highly sensitive, and simultaneous ambient measurements of these species are rather sparse. Here, we present the development of a high-resolution time-of-flight chemical ionization mass spectrometer (HR-ToF-CIMS) method, utilizing protonated ethanol as reagent ions to simultaneously detect atmospheric gaseous amines (C1 to C6) and amides (C1 to C6). This method possesses sensitivities of 5.6–19.4 Hz pptv−1 for amines and 3.8–38.0 Hz pptv−1 for amides under total reagent ion signals of ∼ 0.32 MHz. Meanwhile, the detection limits were 0.10–0.50 pptv for amines and 0.29–1.95 pptv for amides at 3σ of the background signal for a 1 min integration time. Controlled characterization in the laboratory indicates that relative humidity has significant influences on the detection of amines and amides, whereas the presence of organics has no obvious effects. Ambient measurements of amines and amides utilizing this method were conducted from 25 July to 25 August 2015 in urban Shanghai, China. While the concentrations of amines ranged from a few parts per trillion by volume to hundreds of parts per trillion by volume, concentrations of amides varied from tens of parts per trillion by volume to a few parts per billion by volume. Among the C1- to C6-amines, the C2-amines were the dominant species with concentrations up to 130 pptv. For amides, the C3-amides (up to 8.7 ppb) were the most abundant species. The diurnal and backward trajectory analysis profiles of amides suggest that in addition to the secondary formation of amides in the atmosphere, industrial emissions could be important sources of amides in urban Shanghai. During the campaign, photo-oxidation of amines and amides might be a main loss pathway for them in daytime, and wet deposition was also an important sink.

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11

Kutschy, Peter, Pavol Kristian, Milan Dzurilla, Dušan Koščík, and Róbert Nádaskay. "Selectivity of nucleophilic addition to and substitution at isothiocyanatocarbonyl group. Reactions of 4-pentinoyl- and 2-(2-propinyl)-4-pentinoyl isothiocyanate with amines and methanol." Collection of Czechoslovak Chemical Communications 52, no. 4 (1987): 995–1005. http://dx.doi.org/10.1135/cccc19870995.

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4-Pentinoyl isothiocyanate reacts with primary and secondary amines by either nucleophilic addition to N=C=S group to yield the corresponding thioureas, or a nucleophilic substitution at the carbonyl group to give 4-pentinoic acid amides. The less nucleophilic diphenylamine reacts selectively to afford the product of nucleophilic addition only. 2-(2-Propinyl)-4-pentinoyl isothiocyanate, having a sterically hindered carbonyl group, furnished with primary amines a mixture of amides and thioureas, whereas the bulkier secondary amines react selectively to form thioureas only. Both isothiocyanates afford with methanol as a nucleophile exclusively the corresponding O-methyl monothiocarbamates.

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12

Bisai, Milan Kumar, Kritika Gour, Tamal Das, Kumar Vanka, and Sakya S. Sen. "Lithium compound catalyzed deoxygenative hydroboration of primary, secondary and tertiary amides." Dalton Transactions 50, no. 7 (2021): 2354–58. http://dx.doi.org/10.1039/d1dt00364j.

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13

Ueda, Yuki, Shintaro Morisada, Hidetaka Kawakita, and Keisuke Ohto. "Selective Extraction of Platinum(IV) from the Simulated Secondary Resources Using Simple Secondary Amide and Urea Extractants." Separations 8, no. 9 (September 1, 2021): 139. http://dx.doi.org/10.3390/separations8090139.

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The recycling of rare metals such as platinum (Pt) from secondary resources, such as waste electronic and electrical equipment and automotive catalysts, is an urgent global issue. In this study, simple secondary amides and urea, N-(2-ethylhexyl)acetamide, N-(2-ethylhexyl)octanamide, and 1-butyl-3-(2-ethylhexyl)urea, which selectively extract Pt(IV) from a simulated effluent containing numerous metal ions, such as in an actual hydrometallurgical process, were synthesized and achieved efficient Pt(IV) stripping using only water. Comparison of Pt(IV) extraction behavior with a tertiary amide without N–H moieties suggests that the secondary amides and urea extractants effectively use hydrogen bonding to the hexachloroplatinate anion by N–H moieties. Examining the conditions for the third phase formation revealed that the secondary amide extractant with the longest alkyl chain can be used in the extraction process for a long time without forming any third phase, despite its lower Pt(IV) extraction capacity. The practical trial with simple compounds developed in this study should contribute to the development of Pt separation and purification processes.

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14

Huang, Pei-Qiang, and Hui Geng. "Simple, versatile, and chemoselective reduction of secondary amides and lactams to amines with the Tf2O–NaBH4 or Cp2ZrHCl–NaBH4 system." Organic Chemistry Frontiers 2, no. 2 (2015): 150–58. http://dx.doi.org/10.1039/c4qo00317a.

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15

Lee, Byung H., and Michael F. Clothier. "Selective reduction of secondary amides to amines in the presence of tertiary amides." Tetrahedron Letters 40, no. 4 (January 1999): 643–44. http://dx.doi.org/10.1016/s0040-4039(98)02509-x.

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16

Arora, Revika, Satya Paul, and Rajive Gupta. "A mild and efficient procedure for the conversion of aromatic carboxylic esters to secondary amides." Canadian Journal of Chemistry 83, no. 8 (August 1, 2005): 1137–40. http://dx.doi.org/10.1139/v05-134.

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A mild and efficient procedure has been developed for the conversion of aromatic carboxylic esters to secondary amides using reusable Zn dust with microwave heating in the presence of N,N-dimethylformamide or conventional heating by stirring in an oil bath using THF as solvent. Zn dust can be reused several times after simple washing with dil. HCl and distilled water.Key words: aromatic carboxylic esters, aromatic primary amines, secondary amides, Zn dust, microwave activation.

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17

Sureshbabu, Popuri, Sadaf Azeez, Priyanka Chaudhary, and Jeyakumar Kandasamy. "tert-Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions." Organic & Biomolecular Chemistry 17, no. 4 (2019): 845–50. http://dx.doi.org/10.1039/c8ob03010c.

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Transamidation of secondary amides with various amines is demonstrated using tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the desired products in excellent yields.

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18

Kolář, Karel, Rafael Doležal, Natálie Karásková, Nadezhda V. Maltsevskaya, and Šárka Křížková. "Molecular Models in Chemistry Education at University and Upper Secondary School - Structure of Amides." Chemistry-Didactics-Ecology-Metrology 24, no. 1-2 (December 1, 2019): 45–51. http://dx.doi.org/10.2478/cdem-2019-0003.

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Abstract Molecular models derived from results of quantum-chemical calculations present an important category of didactic instruments in chemistry education in upper secondary school and, particularly, at university. These models can be used especially as tools for supporting the students’ understanding by visual learning, which can adequately address complexity of many chemical topics, incorporate appropriate didactic principles, as well as utilize the benefits brought up by the actual information technology. The proposed molecular models are non-trivial examples of didactic application of computational chemistry techniques in illustration of electron interactions in amidic group, namely the interaction of the free electron pair on the nitrogen atom with the carbonyl group and also the interaction of atoms in the amide group with other surrounding atoms in the molecule. By these molecular models it is possible to explain acid-base properties of amides applying knowledge of electron density distribution in the molecules and the resulting electrostatic potential. Presentation of the structure and properties of the amides within education is important also for the reason that amidic functions are involved in many important natural substances (e.g. proteins, peptides, nucleic acids or alkaloids), synthetic macromolecular substances (e.g. Silon) or pharmaceutical preparations (e.g. paracetamol). Molecular models then serve to support better understanding of the structure of these substances and, in relation to it, their properties.

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19

Huang, Pei-Qiang, Qi-Wei Lang, and Yan-Rong Wang. "Mild Metal-Free Hydrosilylation of Secondary Amides to Amines." Journal of Organic Chemistry 81, no. 10 (May 4, 2016): 4235–43. http://dx.doi.org/10.1021/acs.joc.6b00572.

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20

Cheng, Guolin, Weiwei Lv, Changsheng Kuai, Si Wen, and Shangyun Xiao. "Base-promoted amide synthesis from aliphatic amines and ynones as acylation agents through C–C bond cleavage." Chemical Communications 54, no. 14 (2018): 1726–29. http://dx.doi.org/10.1039/c7cc09310a.

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21

McPherson, Christopher G., Nicola Caldwell, Craig Jamieson, Iain Simpson, and Allan J. B. Watson. "Amidation of unactivated ester derivatives mediated by trifluoroethanol." Organic & Biomolecular Chemistry 15, no. 16 (2017): 3507–18. http://dx.doi.org/10.1039/c7ob00593h.

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22

Majewski, Marek, Agnieszka Ulaczyk-Lesanko, and Fan Wang. "Chiral lithium amides on polymer support Synthesis and use in deprotonation of ketones." Canadian Journal of Chemistry 84, no. 2 (February 1, 2006): 257–68. http://dx.doi.org/10.1139/v06-006.

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A number of chiral secondary amines attached to Merrifield resin or to noncrosslinked (soluble) polystyrene support were synthesized. The corresponding lithium amides, generated from these amines by treatment with BuLi, react with tropinone, a model symmetrical ketone, to give the corresponding enolates enantioselectively (ee up to 75%). The enolates were trapped either as the corresponding aldol adducts by a reaction with benzaldehyde or as ring-opening products in a reaction with a chloroformate.Key words: chiral lithium amides, polymer-supported reagents, deprotonation, enolates, tropinone.

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23

Yedage, Subhash L., Denvert S. D'silva, and Bhalchandra M. Bhanage. "MnO2 catalyzed formylation of amines and transamidation of amides under solvent-free conditions." RSC Advances 5, no. 98 (2015): 80441–49. http://dx.doi.org/10.1039/c5ra13094h.

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24

Leggio, A., E. L. Belsito, G. De Luca, M. L. Di Gioia, V. Leotta, E. Romio, C. Siciliano, and A. Liguori. "One-pot synthesis of amides from carboxylic acids activated using thionyl chloride." RSC Advances 6, no. 41 (2016): 34468–75. http://dx.doi.org/10.1039/c5ra24527c.

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25

Sakai, Norio, Masashi Takeoka, Takayuki Kumaki, Hirotaka Asano, Takeo Konakahara, and Yohei Ogiwara. "Indium-catalyzed reduction of secondary amides with a hydrosiloxane leading to secondary amines." Tetrahedron Letters 56, no. 46 (November 2015): 6448–51. http://dx.doi.org/10.1016/j.tetlet.2015.09.148.

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26

Xiao, Kai-Jiong, Ai-E. Wang, and Pei-Qiang Huang. "Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation." Angewandte Chemie International Edition 51, no. 33 (July 13, 2012): 8314–17. http://dx.doi.org/10.1002/anie.201204098.

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27

Xiao, Kai-Jiong, Ai-E. Wang, and Pei-Qiang Huang. "Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation." Angewandte Chemie 124, no. 33 (July 13, 2012): 8439–42. http://dx.doi.org/10.1002/ange.201204098.

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28

Cheng, Chen, and Maurice Brookhart. "Iridium-Catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane." Journal of the American Chemical Society 134, no. 28 (July 6, 2012): 11304–7. http://dx.doi.org/10.1021/ja304547s.

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29

Budynina, Ekaterina, Konstantin Ivanov, Ivan Sorokin, and Mikhail Melnikov. "Ring Opening of Donor–Acceptor Cyclopropanes with N-Nucleophiles." Synthesis 49, no. 14 (May 18, 2017): 3035–68. http://dx.doi.org/10.1055/s-0036-1589021.

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Ring opening of donor–acceptor cyclopropanes with various N-nucleophiles provides a simple approach to 1,3-functionalized compounds that are useful building blocks in organic synthesis, especially in assembling various N-heterocycles, including natural products. In this review, ring-opening reactions of donor–acceptor cyclopropanes with amines, amides, hydrazines, N-heterocycles, nitriles, and the azide ion are summarized.1 Introduction2 Ring Opening with Amines3 Ring Opening with Amines Accompanied by Secondary Processes Involving the N-Center3.1 Reactions of Cyclopropane-1,1-diesters with Primary and Secondary Amines3.1.1 Synthesis of γ-Lactams3.1.2 Synthesis of Pyrroloisoxazolidines and -pyrazolidines3.1.3 Synthesis of Piperidines3.1.4 Synthesis of Azetidine and Quinoline Derivatives3.2 Reactions of Ketocyclopropanes with Primary Amines: Synthesis of Pyrrole Derivatives3.3 Reactions of Сyclopropane-1,1-dicarbonitriles with Primary Amines: Synthesis of Pyrrole Derivatives4 Ring Opening with Tertiary Aliphatic Amines5 Ring Opening with Amides6 Ring Opening with Hydrazines7 Ring Opening with N-Heteroaromatic Compounds7.1 Ring Opening with Pyridines7.2 Ring Opening with Indoles7.3 Ring Opening with Di- and Triazoles7.4 Ring Opening with Pyrimidines8 Ring Opening with Nitriles (Ritter Reaction)9 Ring Opening with the Azide Ion10 Summary

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30

Grbović, Ljubica, Bojana Radovan Vasiljević, Ksenija Pavlović, Timea Hajnal-Jafari, Simonida Đurić, Mirjana Popsavin, and Slavko Kevrešan. "Microwave-assisted synthesis of biologically active amide derivatives of naphthenic acids under neat conditions." Macedonian Journal of Chemistry and Chemical Engineering 37, no. 1 (June 9, 2018): 13. http://dx.doi.org/10.20450/mjcce.2018.1371.

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Within the field of green chemistry, a noticeable results were obtained in the solvent-free synthesis of amide derivatives of naphthenic acids under microwave irradiation. Naphthenic acid amides, anilides, and morpholides were synthesized directly from free carboxylic acids and amines in the absence of solvent and catalyst under high-temperature heating in a closed-vessel system of microwave reactor. With this new and efficient method, different primary, secondary, and tertiary amide derivatives of naphthenic acids were obtained in good to excellent yields. Synthesized derivatives were assayed as plant rooting agents for their stimulative effects on the formation of adventitious roots in sunflower cuttings and susceptibility for growth stimulation of Pseudomonas sp. strains.

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31

Thakkar, Balmukund, John Svendsen, and Richard Engh. "Density Functional Studies on Secondary Amides: Role of Steric Factors in Cis/Trans Isomerization." Molecules 23, no. 10 (September 25, 2018): 2455. http://dx.doi.org/10.3390/molecules23102455.

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Cis/trans isomerization of amide bonds is a key step in a wide range of biological and synthetic processes. Occurring through C-N amide bond rotation, it also coincides with the activation of amides in enzymatic hydrolysis. In recently described QM studies of cis/trans isomerization in secondary amides using density functional methods, we highlighted that a peptidic prototype, such as glycylglycine methyl ester, can suitably represent the isomerization and complexities arising out of a larger molecular backbone, and can serve as the primary scaffold for model structures with different substitution patterns in order to assess and compare the steric effect of the substitution patterns. Here, we describe our theoretical assessment of such steric effects using tert-butyl as a representative bulky substitution. We analyze the geometries and relative stabilities of both trans and cis isomers, and effects on the cis/trans isomerization barrier. We also use the additivity principle to calculate absolute steric effects with a gradual increase in bulk. The study establishes that bulky substitutions significantly destabilize cis isomers and also increases the isomerization barrier, thereby synergistically hindering the cis/trans isomerization of secondary amides. These results provide a basis for the rationalization of kinetic and thermodynamic properties of peptides with potential applications in synthetic and medicinal chemistry.

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32

Lee, Byung H., and Michael F. Clothier. "ChemInform Abstract: Selective Reduction of Secondary Amides to Amines in the Presence of Tertiary Amides." ChemInform 30, no. 16 (June 16, 2010): no. http://dx.doi.org/10.1002/chin.199916070.

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33

Gu, Jiajia, Zheng Fang, Yuhang Yang, Zhao Yang, Li Wan, Xin Li, Ping Wei, and Kai Guo. "Copper-catalyzed one-pot oxidative amidation of alcohol to amide via C–H activation." RSC Advances 6, no. 92 (2016): 89413–16. http://dx.doi.org/10.1039/c6ra20732d.

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Copper-catalyzed one-pot oxidative amidation of both aliphatic and aromatic alcohols with N-chloramines, prepared in situ from many types of primary and secondary amines, to form amides under mild conditions.

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34

Kada, Rudolf, Jarmila Bruncková, and Pavol Bobál'. "Reaction of Ethyl 5-Substituted-2-furoylmalonates with Secondary Amines." Collection of Czechoslovak Chemical Communications 59, no. 6 (1994): 1400–1407. http://dx.doi.org/10.1135/cccc19941400.

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In situ prepared magnesium salts of ethyl malonate react with 5-X-2-furoyl chlorides (X = Br, NO2, C6H5S and C6H5SO2) to give the corresponding ethyl 5-X-2-furoylmalonates. On treatment of these compounds with secondary amines no nucleophilic substitution of the group X in position 5 of the furan nucleus took place but, instead, amides of 5-X-2-furancarboxylic acids were isolated.

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35

Thakur, Neerja, Nikhil Sharma, Vijay Kumar, and Tek Chand Bhalla. "Computational Analysis of the Primary and Secondary Structure of Amidases in Relation to their pH Adaptation." Current Proteomics 17, no. 2 (January 30, 2020): 95–106. http://dx.doi.org/10.2174/1570164616666190718150627.

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Background: Amidases are ubiquitous enzymes and biological functions of these enzymes vary widely. They are considered to be synergistically involved in the synthesis of a wide variety of carboxylic acids, hydroxamic acids and hydrazides, which find applications in commodity chemicals synthesis, pharmaceuticals agrochemicals and wastewater treatments. Methods: They hydrolyse a wide variety of amides (short-chain aliphatic amides, mid-chain amides, arylamides, α-aminoamides and α-hydroxyamides) and can be grouped on the basis of their catalytic site and preferred substrate. Despite their economic importance, we lack knowledge as to how these amidases withstand elevated pH and temperature whereas others cannot. Results: The present study focuses on the statistical comparison between the acid-tolerant, alkali tolerant and neutrophilic organisms. In silico analysis of amidases of acid-tolerant, alkali tolerant and neutrophilic organisms revealed some striking trends as to how amino acid composition varies significantly. Statistical analysis of primary and secondary structure revealed amino acid trends in amidases of these three groups of bacteria. The abundance of isoleucine (Ile, I) in acid-tolerant and leucine (Leu, L) in alkali tolerant showed the aliphatic amino acid dominance in extreme conditions of pH in acidtolerant and alkali tolerant amidases. Conclusion: The present investigation insights physiochemical properties and dominance of some crucial amino acid residues in the primary and secondary structure of some amidases from acid-tolerant, alkali tolerant and neutrophilic microorganisms.

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Chandrasekaran, Srinivasan, and Rajagopal Ramkumar. "Catalyst-Free, Metal-Free, and Chemoselective Transamidation of Activated Secondary Amides." Synthesis 51, no. 04 (October 18, 2018): 921–32. http://dx.doi.org/10.1055/s-0037-1610664.

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A simple protocol, which is catalyst-free, metal-free, and chemoselective, for transamidation of activated secondary amides in ethanol as solvent under mild conditions is reported. A wide range of amines, amino acids, amino alcohols, and the substituents, which are problematic in catalyzed transamidation, are tolerated in this methodology. The transamidation reaction was successfully extended to water as the medium as well. The present methodology appears to be better than the other catalyzed transamidations reported recently.

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37

Wen, Xue-Ping, Yu-Ling Han, and Jian-Xin Chen. "Nickel-catalyzed aminocarbonylation of aryl halides using carbamoylsilane as an amide source." RSC Advances 7, no. 71 (2017): 45107–12. http://dx.doi.org/10.1039/c7ra08009c.

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The nickel-catalyzed aminocarbonylation reaction of aryl halides using carbamoylsilanes as an amide source in toluene is developed leading to the formation of some tertiary or secondary aryl amides in good yields.

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Gong, Hang, Juan Ma, and Jingyu Zhang. "Mn(II)-Catalyzed N-Acylation of Amines." Synthesis 51, no. 03 (September 4, 2018): 693–703. http://dx.doi.org/10.1055/s-0037-1610267.

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A practical protocol has been developed here for the Mn(II)-catalyzed N-acylation of amines with high yields using N,N-dimethylformamide and other amides as the carbonyl source. The protocol is simple, does not require any acid, base, ligand, or other additives, and encompasses a broad substrate scope for primary, secondary, and heterocyclic amines.

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Tokuyama, Hidetoshi, Suguru Itabashi, Masashi Shimomura, Manabu Sato, Hiroki Azuma, Kentaro Okano, and Juri Sakata. "One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (–)-Castoramine." Synlett 29, no. 13 (June 26, 2018): 1786–90. http://dx.doi.org/10.1055/s-0037-1610435.

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A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (–)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.

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40

Nodzewska, Aneta, Agnieszka Wadolowska, Katarzyna Podgorska, Damian Pawelski, and Ryszard Lazny. "Synthesis of Solid-phase Supported Chiral Amines and Investigation of Stereoselectivity of Aldol Reactions of Amine-free Tropinone Enolate." Current Organic Chemistry 23, no. 17 (November 2, 2019): 1867–79. http://dx.doi.org/10.2174/1385272823666190916145332.

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Seven selected chiral mono-, di-, and tridentate amines supported on insoluble polymer were effectively prepared from corresponding primary amines or secondary amino alcohols and Merrifield resin. The reaction of the polymer-supported amines with excess n-butyllithium gave the corresponding lithium amide bases, which were tested in the aldol reactions of tropinone with benzaldehyde. The deprotonation reactions were carried out with or without separation of the lithium enolate from polymer-supported reagents. Using the procedure with separation of lithium enolate from supported chiral reagent different results were obtained with or without the addition of LiCl despite the fact that aggregate formation of Merrifield resin supported Li-amides is hindered. Without the additive, the aldol products were obtained in low diastereoselectivity and enantioselectivity, whereas the addition of LiCl resulted in a significant increase of de and ee even when LiCl was added after the deprotonation step and separation of the chiral amine.

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41

Arnold, Zdeněk, Miloš Buděšínský, and Magdalena Pánková. "Reactivity of triformylmethane. I. Reactions of triformylmethane with selected types of amino compounds." Collection of Czechoslovak Chemical Communications 56, no. 5 (1991): 1019–31. http://dx.doi.org/10.1135/cccc19911019.

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Reactions of triformylmethane with various types of amino compounds were investigated. Besides with ammonia, triformylmethane reacts spontaneously with primary amines, aminoacids and their esters, urea and related compounds including carbamic acid derivatives. Reactions with amides of carboxylic and sulfonic acids require catalysis with Lewis acids. Primary products are aminomethylenemalonaldehyde derivatives IIIa-IIIv. Reactions of triformylmethane with excess of selected primary amines and two secondary amines (dimethylamine and morpholine) were also studied.

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42

Cheng, Chen, and Maurice Brookhart. "ChemInform Abstract: Iridium-Catalyzed Reduction of Secondary Amides to Secondary Amines and Imines by Diethylsilane." ChemInform 44, no. 1 (January 1, 2013): no. http://dx.doi.org/10.1002/chin.201301067.

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Xiao, Kai-Jiong, Ai-E. Wang, and Pei-Qiang Huang. "ChemInform Abstract: Direct Transformation of Secondary Amides into Secondary Amines: Triflic Anhydride Activated Reductive Alkylation." ChemInform 44, no. 5 (January 29, 2013): no. http://dx.doi.org/10.1002/chin.201305052.

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44

Sakai, Norio, Masashi Takeoka, Takayuki Kumaki, Hirotaka Asano, Takeo Konakahara, and Yohei Ogiwara. "ChemInform Abstract: Indium-Catalyzed Reduction of Secondary Amides with a Hydrosiloxane Leading to Secondary Amines." ChemInform 47, no. 12 (March 2016): no. http://dx.doi.org/10.1002/chin.201612049.

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45

Huang, Pei-Qiang, Qi-Wei Lang, Ai-E. Wang, and Jian-Feng Zheng. "Direct reductive coupling of secondary amides: chemoselective formation of vicinal diamines and vicinal amino alcohols." Chemical Communications 51, no. 6 (2015): 1096–99. http://dx.doi.org/10.1039/c4cc08330j.

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We report the first direct and chemoselective reductive homocoupling reaction of secondary amides and cross-coupling reaction of secondary amides with ketones. This method relies on the direct generation of α-amino carbon radicals from amides.

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46

Maslivetc, Vladimir A., Marina Rubina, and Michael Rubin. "One-pot synthesis of GABA amides via the nucleophilic addition of amines to 3,3-disubstituted cyclopropenes." Organic & Biomolecular Chemistry 13, no. 34 (2015): 8993–95. http://dx.doi.org/10.1039/c5ob01462j.

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A one-pot synthesis of various GABA amides has been demostrated, employing the nucleophilic addition of primary and secondary amines across the double bond of cyclopropene-3-carboxamides, followed by ring-opening of the resulting donor–acceptor cyclopropanes and subsequent in situ reduction of enamine intermediates.

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Lampland, Nicole L., Megan Hovey, Debabrata Mukherjee, and Aaron D. Sadow. "Magnesium-Catalyzed Mild Reduction of Tertiary and Secondary Amides to Amines." ACS Catalysis 5, no. 7 (June 12, 2015): 4219–26. http://dx.doi.org/10.1021/acscatal.5b01038.

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48

Das, Shoubhik, Daniele Addis, Kathrin Junge, and Matthias Beller. "Zinc-Catalyzed Chemoselective Reduction of Tertiary and Secondary Amides to Amines." Chemistry - A European Journal 17, no. 43 (September 13, 2011): 12186–92. http://dx.doi.org/10.1002/chem.201101143.

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49

Böttcher, Tobias, and Cameron Jones. "Extremely bulky secondary phosphinoamines as substituents for sterically hindered aminosilanes." Dalton Transactions 44, no. 33 (2015): 14842–53. http://dx.doi.org/10.1039/c5dt02504d.

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The synthesis of a series of extremely bulky secondary amines with a phosphine function, Ar^†(PR₂)NH (Ar^†= C₆H₂{C(H)Ph₂}₂Prⁱ-2,6,4; R = Ph, NEt₂, NPrⁱ₂) is described. Deprotonation with eithern-BuLi or KH yields the respective alkali metal amides. Reactions with a series of chlorosilanes allows access to monomeric molecular compounds bearing the extremely bulky amino substituentsviasalt elimination.

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50

Kolesov, Boris A. "Raman spectra of crystalline secondary amides." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 179 (May 2017): 216–20. http://dx.doi.org/10.1016/j.saa.2017.02.046.

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