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Journal articles on the topic 'Leuckart Reaction'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

Umar, Qasim, and Mei Luo. "A Brief Review: Advancement in the Synthesis of Amine through the Leuckart Reaction." Reactions 4, no. 1 (2023): 117–47. http://dx.doi.org/10.3390/reactions4010007.

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This review presents a summary of reactions that take place during the “Leuckart-type reaction”. The significance of, as well as recent advancements in, the synthesis of amines through simple and inexpensive methods using readily available raw materials is discussed. This review includes all catalytic and noncatalytic reactions that involve the Leuckart method. Recent studies have shown that at least a quarter of C–N bond-forming reactions in the pharmaceutical industry are occur with the support of reductive amination. Recently, experimental conditions have achieved excellent yields. The “Leu

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2

Bokale-Shivale, Suvarna, Mohammad A. Amin, Rajiv T. Sawant, et al. "Synthesis of substituted 3,4-dihydroquinazolinones via a metal free Leuckart–Wallach type reaction." RSC Advances 11, no. 1 (2021): 349–53. http://dx.doi.org/10.1039/d0ra10142g.

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3

Lejon, Tore, Irene Helland, Wang Liufang, et al. "Effect of Formamide in the Leuckart Reaction." Acta Chemica Scandinavica 53 (1999): 76–78. http://dx.doi.org/10.3891/acta.chem.scand.53-0076.

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4

Tournier, Lucie, and Samir Z. Zard. "A practical variation on the Leuckart reaction." Tetrahedron Letters 46, no. 6 (2005): 971–73. http://dx.doi.org/10.1016/j.tetlet.2004.12.042.

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5

Dai, Zengjin, Ying-Min Pan, Shou-Guo Wang, Xumu Zhang, and Qin Yin. "Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(iii) complexes bearing an amidato ligand." Organic & Biomolecular Chemistry 19, no. 41 (2021): 8934–39. http://dx.doi.org/10.1039/d1ob01710a.

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6

M., L. SHARMA, K. TALWAR K., GUPTA ANU, and KISHORE LALIT. "Synthesis of Quaternary Salts of Ammonia from Aromatic Aldehydes via Leuckart Reaction and their Plant Growth Retardant Activity." Journal of Indian Chemical Society Vol. 74, Mar 1997 (1997): 233–34. https://doi.org/10.5281/zenodo.5889777.

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Department of Chemistry, Department of Mathematics & Statistics, Punjab Agricultural University, Ludhiana-141 004 <em>Manuscript received 23 February 1995, revised 28 August 1995, accepted 17 October 1995</em> Synthesis of Quaternary Salts of Ammonia from Aromatic Aldehydes via Leuckart Reaction and their Plant Growth Retardant Activity.

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7

Frederick, Michael O., and Douglas P. Kjell. "A synthesis of abemaciclib utilizing a Leuckart–Wallach reaction." Tetrahedron Letters 56, no. 7 (2015): 949–51. http://dx.doi.org/10.1016/j.tetlet.2014.12.082.

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8

Maldonado, I. C. A. Romero, and G. A. Nikiforov. "Leuckart reaction for quinoid derivatives of 2,6-di-tert-butylphenol." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 36, no. 10 (1987): 2184–85. http://dx.doi.org/10.1007/bf00962022.

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9

Bannikov, G. F., G. A. Nikiforov, and V. V. Ershov. "Leuckart reaction of carbonyl derivatives of 2,6-di-tert-butylphenol." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 6 (1985): 1289–91. http://dx.doi.org/10.1007/bf00956104.

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10

Adger, Brian M., Ulrich C. Dyer, Ian C. Lennon, Peter D. Tiffin, and Simon E. Ward. "A novel synthesis of tert-leucine via a Leuckart type reaction." Tetrahedron Letters 38, no. 12 (1997): 2153–54. http://dx.doi.org/10.1016/s0040-4039(97)00269-4.

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11

Skachilova, S. Ya, N. K. Zheltukhin, V. N. Sergeev, and N. K. Davydova. "Reductive Amination of Sterically Hindered Arylaminoketones Using a Modified Leuckart Reaction." Pharmaceutical Chemistry Journal 52, no. 6 (2018): 545–49. http://dx.doi.org/10.1007/s11094-018-1857-7.

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12

Frederick, Michael O., and Douglas P. Kjell. "ChemInform Abstract: A Synthesis of Abemaciclib Utilizing a Leuckart-Wallach Reaction." ChemInform 46, no. 24 (2015): no. http://dx.doi.org/10.1002/chin.201524228.

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13

Awachie, Peter I., and Vincent C. Agwada. "Evidence for rate limiting C-H bond cleavage in the leuckart reaction." Tetrahedron 46, no. 6 (1990): 1899–910. http://dx.doi.org/10.1016/s0040-4020(01)89758-1.

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14

Loupy, André, Daphné Monteux, Alain Petit, Jesús Ma Aizpurua, Esther Domínguez, and Claudio Palomo. "Towards the rehabilitation of the Leuckart reductive amination reaction using microwave technology." Tetrahedron Letters 37, no. 45 (1996): 8177–80. http://dx.doi.org/10.1016/0040-4039(96)01865-5.

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15

Carlson, Rolf, Tore Lejon, Torbjörn Lundstedt, et al. "An Optimized Procedure for the Reductive Amination of Acetophenone by the Leuckart Reaction." Acta Chemica Scandinavica 47 (1993): 1046–49. http://dx.doi.org/10.3891/acta.chem.scand.47-1046.

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16

Dom地guez, Esther, Mar誕 Jes徭 Villa, Ester Dom地guez, and Ester Lete. "On the Leuckart Reaction of Deoxybenzoins. Isolation and Characterization of 2,3,4,5-Tetraarypyridine Derivatives." HETEROCYCLES 24, no. 7 (1986): 1943. http://dx.doi.org/10.3987/r-1986-07-1943.

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17

Aguilar-Bolados, Héctor, Daniela Vargas-Astudillo, Mehrdad Yazdani-Pedram, et al. "Facile and Scalable One-Step Method for Amination of Graphene Using Leuckart Reaction." Chemistry of Materials 29, no. 16 (2017): 6698–705. http://dx.doi.org/10.1021/acs.chemmater.7b01438.

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18

Frederick, Michael O., Mark A. Pietz, Douglas P. Kjell, et al. "Development of a Leuckart–Wallach Reaction in Flow for the Synthesis of Abemaciclib." Organic Process Research & Development 21, no. 9 (2017): 1447–51. http://dx.doi.org/10.1021/acs.oprd.7b00234.

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19

ADGER, B. M., U. C. DYER, I. C. LENNON, P. D. TIFFIN, and S. E. WARD. "ChemInform Abstract: A Novel Synthesis of tert-Leucine via a Leuckart Type Reaction." ChemInform 28, no. 26 (2010): no. http://dx.doi.org/10.1002/chin.199726243.

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20

Song, Man, Leili Tahershamsi, Jie Zhao, Zhibin Zhang, and Helena Grennberg. "Efficient Gelation of Graphene Oxide Aqueous Dispersion Induced by Sonication-Promoted Leuckart Reaction." ChemNanoMat 4, no. 11 (2018): 1145–52. http://dx.doi.org/10.1002/cnma.201800286.

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21

Schofield, Kevin, Shayna Maddern, Yueteng Zhang, et al. "Deuterated reagents in multicomponent reactions to afford deuterium-labeled products." Beilstein Journal of Organic Chemistry 20 (September 6, 2024): 2270–79. http://dx.doi.org/10.3762/bjoc.20.195.

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The utility of bio-isosteres is broad in drug discovery and methodology herein enables the preparation of deuterium-labeled products is the most fundamental of known bio-isosteric replacements. As such we report the use of both [D1]-aldehydes and [D2]-isonitriles across 8 multicomponent reactions (MCRs) to give diverse arrays of deuterated products. A highlight is the synthesis of several FDA-approved calcium channel blockers, selectively deuterated at a t1/2 limiting metabolic soft-spot via use of [D1]-aldehydes. Surrogate pharmacokinetic analyses of microsomal stability confirm prolongation

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22

Jílek, Jiří, Jiří Urban, Petr Taufmann, et al. "Potential antidepressants: 2-(Phenylthio)aralkylamines." Collection of Czechoslovak Chemical Communications 54, no. 7 (1989): 1995–2008. http://dx.doi.org/10.1135/cccc19891995.

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Reactions of 2-(phenylthio)benzyl chloride with dimethylamine, diethylamine, pyrrolidine, piperidine, morpholine, and 1-methylpiperazine afforded the title compounds VI-XI. Reaction of 2-(phenylthio)benzaldehyde with nitromethane gave the nitrostyrene XIV which was reduced with lithium aluminium hydride to 2-(2-(phenylthio)phenyl)ethylamine (XVI). This was transformed to the N-methyl and N,N-dimethyl derivatives XVIII and XIX. The Claisen reaction of (2-(phenylthio)phenyl)acetonitrile with ethyl acetate afforded compound XXI which was cleaved by phosphoric acid to (2-(phenylthio)phenyl)acetone

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23

Garcı́a Martı́nez, Antonio, Enrique Teso Vilar, Amelia Garcı́a Fraile, and Paloma Martı́nez-Ruiz. "About the Leuckart reaction of chiral 2-norbornanones bearing electron-withdrawing groups: reaction of bridgehead triflates and triflamides." Tetrahedron 59, no. 9 (2003): 1565–69. http://dx.doi.org/10.1016/s0040-4020(03)00037-1.

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24

Xu, Guangming, Bo Chen, Hua Wang, Yinzhuang Chen, Li Ding, and Shouzhuo Yao. "Detection of intermediates in Leuckart reaction by desorption corona beam ionization ambient mass spectrometry." Analytical Methods 4, no. 10 (2012): 3098. http://dx.doi.org/10.1039/c2ay25588j.

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25

LOUPY, A., D. MONTEUX, A. PETIT, J. M. AIZPURUA, E. DOMINGUEZ, and C. PALOMO. "ChemInform Abstract: Towards the Rehabilitation of the Leuckart Reductive Amination Reaction Using Microwave Technology." ChemInform 28, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199708064.

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26

Lee, Sung-Chan, and Seung Bum Park. "Novel application of Leuckart–Wallach reaction for synthesis of tetrahydro-1,4-benzodiazepin-5-ones library." Chemical Communications, no. 36 (2007): 3714. http://dx.doi.org/10.1039/b709768a.

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27

Martı́nez, Antonio Garcı́a, Enrique Teso Vilar, Amelia Garcı́a Fraile, and Paloma Martı́nez-Ruiz. "Enantioselective synthesis of both enantiomers of vicinal norbornanediamines through the Leuckart reaction of 2-norbornanones." Tetrahedron: Asymmetry 12, no. 15 (2001): 2153–58. http://dx.doi.org/10.1016/s0957-4166(01)00376-7.

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28

Šindelář, Karel, Vojtěch Kmoníček, Marta Hrubantová, and Zdeněk Polívka. "Substituted N,N-Dimethyl-3-(phenylthio)- and -4-(phenylthio)benzylamines." Collection of Czechoslovak Chemical Communications 57, no. 1 (1992): 194–203. http://dx.doi.org/10.1135/cccc19920194.

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(Arylthio)benzoic acids IIa - IIe and VIb - VId were transformed via the acid chlorides to the N,N-dimethylamides which were reduced either with diborane "in situ" or with lithium aluminium hydride to N,N-dimethyl-(arylthio)benzylamines Ia - Ie and Vb - Vd. Leuckart reaction of the aldehydes IX and X with dimethylformamide and formic acid afforded directly the amines Va and Ve. Demethylation of the methoxy compounds Ia and Ve with hydrobromic acid resulted in the phenolic amines If and Vf. The most interesting N,N-dimethyl-4-(phenylthio)benzylamine (Va) hydrochloride showed affinity to choline

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29

Fülöp, Ferenc, Kalevi Pihlaja, Jorma Mattinen, and Gábor Bernáth. "A new aspect of the leuckart reaction: Synthesis of 1-methyl and/or 3-hydroxymethyl-1,3-heterocycles." Tetrahedron Letters 28, no. 1 (1987): 115–16. http://dx.doi.org/10.1016/s0040-4039(00)95664-8.

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30

Martinez, Antonio Garcia, Enrique Teso Vilar, Amelia Garcia Fraile, and Paloma Martinez-Ruiz. "ChemInform Abstract: Enantioselective Synthesis of Both Enantiomers of Vicinal Norbornanediamines Through the Leuckart Reaction of 2-Norbornanones." ChemInform 33, no. 7 (2010): no. http://dx.doi.org/10.1002/chin.200207073.

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31

García Martínez, Antonio, Enrique Teso Vilar, Amelia García Fraile, and Paloma Martínez-Ruiz. "Influence of the Bridgehead Substituent on the Stereoselective Leuckart Reaction of 2-Norbornanones − Skeletal Rearrangement versus Structural Retention." European Journal of Organic Chemistry 2001, no. 15 (2001): 2805. http://dx.doi.org/10.1002/1099-0690(200108)2001:15<2805::aid-ejoc2805>3.0.co;2-g.

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32

Barba, Fructuoso, Javier Recio, and Belen Batanero. "Microwave-assisted conversion of carbonyl compounds into formylated secondary amines: new contribution to the Leuckart reaction mechanism in N-methylformamide." Tetrahedron Letters 54, no. 14 (2013): 1835–38. http://dx.doi.org/10.1016/j.tetlet.2013.01.097.

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33

SHARMA, M. L., K. K. TALWAR, A. GUPTA, and L. KISHORE. "ChemInform Abstract: Synthesis of Quaternary Salts of Ammonia from Aromatic Aldehydes via Leuckart Reaction and Their Plant Growth Retardant Activity." ChemInform 29, no. 25 (2010): no. http://dx.doi.org/10.1002/chin.199825103.

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34

Pan, Xianhua, Dongxian Zhao, Yao Shi, Youyou Huang, Siyu Chen, and Feng Liu. "Synthesis of S-3-Hydroxyadamantylglycine Ester by a Pd/C Promoted Mild Leuckart-Wallach Reaction and an L-Dibenzoyltartaric Acid Resolution." Journal of Chemical Research 39, no. 2 (2015): 108–11. http://dx.doi.org/10.3184/174751915x14227074676509.

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35

Muzalevskiy, Vasiliy M., Valentine G. Nenajdenko, Aleksey V. Shastin, Elizabeth S. Balenkova та Günter Haufe. "Synthesis of trifluoromethyl alcohols from tert-butoxy-β-(trifluoromethyl)styrenes and trifluoromethylbenzyl ketones under the conditions of the Leuckart–Wallach reaction". Journal of Fluorine Chemistry 129, № 10 (2008): 1052–55. http://dx.doi.org/10.1016/j.jfluchem.2008.06.014.

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36

Garcı́a Martı́nez, A., E. Teso Vilar, A. Garcı́a Fraile, P. Martı́nez Ruiz, R. Macı́as San Antonio, and M. P. Martı́nez Alcázar. "On the mechanism of the Leuckart reaction. Enantiospecific preparation of (1R,2R)- and (1S,2S)-N-(3,3-dimethyl-2-formylamino-1-norbornyl)acetamide." Tetrahedron: Asymmetry 10, no. 8 (1999): 1499–505. http://dx.doi.org/10.1016/s0957-4166(99)00125-1.

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37

Oforka, Linda C., Monsuru A. Adeleke, Joseph C. Anikwe, et al. "Biting Rates and Onchocerca Infectivity Status of Black Flies from the Simulium damnosum Complex (Diptera: Simuliidae) in Osun State, Nigeria." Journal of Medical Entomology 57, no. 3 (2020): 901–7. http://dx.doi.org/10.1093/jme/tjz250.

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Abstract The Simulium damnosum Theobald complex transmits Onchocerca volvulus Leuckart (Spirurida: Onchocercidae), the causative agent of onchocerciasis. Recent evidence suggests that control efforts have strongly suppressed parasite populations, but vector surveillance is needed in parts of Africa where the disease remains endemic. Here, studies on biting rates and infectivity status of suspected vector species were conducted in three onchocerciasis-endemic areas, namely Iwo, Ede, and Obokun, in Osun State, Nigeria. A total of 3,035 black flies were collected between October 2014 and Septembe

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38

Garcia Martinez, A., E. Teso Vilar, A. Garcia Fraile, P. Martinez Ruiz, R. Macias San Antonio, and M. P. Martinez Alcazar. "ChemInform Abstract: On the Mechanism of the Leuckart Reaction. Enantiospecific Preparation of (1R,2R)- and (1S,2S)-N-(3,3-Dimethyl-2-formylamino-1-norbornyl)acetamide." ChemInform 30, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199933100.

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39

Ostovari, Hoda, Ehsan Zahedi, Iraj Sarvi, and Abolfazl Shiroudi. "Kinetic and mechanistic insight into the formation of amphetamine using the Leuckart–Wallach reaction and interaction of the drug with GpC·CpG base-pair step of DNA: a DFT study." Monatshefte für Chemie - Chemical Monthly 149, no. 6 (2018): 1045–57. http://dx.doi.org/10.1007/s00706-018-2145-7.

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40

Pichler, Arthur, Tina L. Walters, Marc E. Frischer, Jens C. Nejstgaard, and Radka Ptáčníková. "Application of species-specific primers to estimate the in situ diet of Bythotrephes [Cladocera, Onychopoda] in its native European range via molecular gut content analysis." Journal of Plankton Research 43, no. 6 (2021): 945–56. http://dx.doi.org/10.1093/plankt/fbab070.

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Abstract The study of invasive species often focuses on regions of recent introduction rather than native habitats. Understanding an invasive species in its natural environment, however, can provide important insights regarding the long-term outcome of invasions. In this study we investigated the diet of the invasive spiny water flea, Bythotrephes longimanus, in two Austrian perialpine lakes, where it is native. The gut contents of wild-caught Bythotrephes individuals were estimated by quantitative polymerase chain reaction, targeting species-specific fragments of the barcoding region of the c

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41

Brewer, Alice R. E. "ChemInform Abstract: Leuckart-Wallach Reaction." ChemInform 39, no. 36 (2008). http://dx.doi.org/10.1002/chin.200836256.

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42

Tournier, Lucie, and Samir Z. Zard. "A Practical Variation on the Leuckart Reaction." ChemInform 36, no. 22 (2005). http://dx.doi.org/10.1002/chin.200522037.

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43

ROMERO MALDONADO, I. K. A., and G. A. NIKIFOROV. "ChemInform Abstract: Leuckart Reaction with Quinoid Derivatives of 2,6-Di-tert-butylphenol." ChemInform 19, no. 18 (1988). http://dx.doi.org/10.1002/chin.198818156.

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44

Kang, Chin-Lun, Chris Hnatyk, Alexa R. Heaton, et al. "A simplified, green synthesis of tertiary amines using the Leuckart-Wallach reaction in subcritical water." Tetrahedron Letters, August 2022, 154079. http://dx.doi.org/10.1016/j.tetlet.2022.154079.

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45

VILLA, M. J., E. DOMINGUEZ, and E. LETE. "ChemInform Abstract: On the Leuckart Reaction of Deoxybenzoins. Isolation and Characterization of 2,3,4,5-Tetraarylpyridine Derivatives." Chemischer Informationsdienst 17, no. 47 (1986). http://dx.doi.org/10.1002/chin.198647200.

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46

Salunke, Jeetendra Y., and Ganapati D. Yadav. "Lanthanum doped zirconia as an efficient catalyst for reductive amination of 2-methoxybenzaldehyde with dimethylformamide via Leuckart type reaction." ES Materials & Manufacturing, 2023. http://dx.doi.org/10.30919/esmm5f853.

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47

"Search of new luminophores with predetermined physicochemical and chemical properties ХVІ. N-arylmethylene- and N–hetarylmethylene- substituted for polyvinylamine". Kharkov University Bulletin Chemical Series, № 31 (2018). http://dx.doi.org/10.26565/2220-637x-2018-31-04.

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Investigation of transformation of polyacrylamide (PAA) in the polyvinylamine (РVAm) the reaction of Hofmann and further transformation of NH2-groups polymer by the Leuckart—Wallach reaction. The reliability of the transformation of PAA into PVAm is confirmed by the reaction of diazotization and acylation of the samples obtained by PVA and by the color reactions of the PVAm transformation products. The structure of PVAm is also confirmed by data from IR spectroscopy and pH-metric titration. The product obtained is a vinylamine copolymer (up to 80%), acrylamide and acrylic acid. Syntheses of N-

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48

FUELOEP, F., K. PIHLAJA, J. MATTINEN, and G. BERNATH. "ChemInform Abstract: Stereochemical Studies. Part 124. A New Aspect of the Leuckart Reaction: Synthesis of 1-Methyl and/or 3-Hydroxymethyl-1,3-heterocycles." ChemInform 18, no. 23 (1987). http://dx.doi.org/10.1002/chin.198723189.

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49

Muzalevskiy, Vasiliy M., Valentine G. Nenajdenko, Aleksey V. Shastin, Elizabeth S. Balenkova та Guenter Haufe. "ChemInform Abstract: Synthesis of Trifluoromethyl Alcohols from tert-Butoxy-β-(trifluoromethyl)styrenes and Trifluoromethylbenzyl Ketones under the Conditions of the Leuckart-Wallach Reaction." ChemInform 40, № 6 (2009). http://dx.doi.org/10.1002/chin.200906083.

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50

"Search for new luminophores with predetermined physicochemical and chemical properties. XIV.N-Arylmethylene- and N-hetarylmethylene derivatives of poly (3‒aminopropene)." Kharkov University Bulletin Chemical Series, no. 34 (2020). http://dx.doi.org/10.26565/2220-637x-2020-34-04.

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The possibility of creating polymers with fluorescence, derivatives of poly (3-aminopropene) (PAP) by alkylation of amino groups with aromatic or heterocyclic aldehydes by Leykart-Wallach reaction with own fluorescence was investigated. Synthesis of N-alkylated PAP derivatives was performed by sequential conversion: acrylamide → PAA (Mν = 100 kDa) → PAP → alkylated PAP. Due to the impossibility of using LiAlH4 to reduce the amide groups of polyacrylamide to amine due to the low solubility of PAA in the non-aqueous (diethyl ether, tetrahydrofuran, etc.) solvents, the reduction of PAA by other r

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