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Journal articles on the topic 'Aminomethylation'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Roman, Gheorghe. "2-Naphthol-pyrazole conjugates as substrates in the Mannich reaction." Zeitschrift für Naturforschung B 73, no. 5 (2018): 275–80. http://dx.doi.org/10.1515/znb-2017-0209.

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AbstractSeveral novel 2-naphthol-pyrazole conjugates have been synthesized through the O-alkylation of 1-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]naphthalen-2-ol with methyl iodide, benzyl chloride, methyl bromoacetate and N-benzyl-2-bromoacetamide. The aminomethylation of these 2-naphthol-pyrazole conjugates has been examined employing the classical conditions for the Mannich reaction, and also by using N,N-dimethylmethyleneiminium chloride as preformed aminomethylating reagent. In both situations, aminomethylation of these substrates occurred at C-4 of the pyrazole ring. The bifunctional substr

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2

Chen, Jia-Rong, Dong Liang, and Wen-Jing Xiao. "Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions." Synthesis 52, no. 17 (2020): 2469–82. http://dx.doi.org/10.1055/s-0040-1707160.

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1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.1 Introduction2 Aminomethylations with 1,3,5-Triazinanes3 Cycloadditions with 1,3,

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3

Agamaliyeva, M. M., A. M. Pashajanov, T. M. Ismailov, N. I. Ismailov, and G. O. Hasanova. "AMINOMETHYLATION OF DIHYDROXYACETOPHENONES." Azerbaijan Chemical Journal, no. 3 (September 22, 2022): 81–86. http://dx.doi.org/10.32737/0005-2531-2022-3-81-86.

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Aminomethylation of trifunctional 2.5-dihydroxyacetophenone (2.5-DHA) and 2.4-dihydro¬xy¬aceto-phenone (2.4-DHA) by free primary and secondary amines in the presence of formaldehyde has been conducted for the first time. It has been established that 2.5-DHA is aminomethylated with secondary heterocyclic amines - piperidine and morpholine and with aqueous formaldehyde solution in alcohol medium at 500C. The reaction proceeds simultaneously via all three functions forming stable C,O-substitution products − β-amino-2-aminomethoxy-4-aminomethyl-5-hydroxypropiophenones. The aminomethylation reactio

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4

Belykh, Dmitri V., Irina S. Tarabukina, Ivan V. Gruzdev, Mikhail I. Kodess, and Aleksandr V. Kutchin. "Aminomethylation of chlorophyll a derivatives using bis(N,N-dimethylamino)methane." Journal of Porphyrins and Phthalocyanines 13, no. 08n09 (2009): 949–56. http://dx.doi.org/10.1142/s1088424609001133.

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Bis(N,N-dimethylamino)methane has been shown to be a convenient reagent for the aminomethylation of chlorophyll a derivatives. Methylpheophorbide a (in enol form) and chlorin e 6 13-amides were aminomethylated with bis(N,N-dimethylamino)methane. Reactivity of methylpheophorbide a exo-ring and chlorin e 6 13-amides vinyl group were shown to be different. Selective methylpheophorbide a exo-ring aminomethylation was realized and isomerization of the exo-ring aminomethylation product with rhodochlorin 15-acrylic derivative formation was studied. The action of bis(N,N-dimethylamino)-methane in the

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5

Ramsh, S. M., E. S. Khrabrova, and L. P. Shamina. "Aminomethylation of pemoline." Chemistry of Heterocyclic Compounds 26, no. 12 (1990): 1387–91. http://dx.doi.org/10.1007/bf00473969.

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6

Nifant’ev, E. E., S. E. Mosyurov, T. S. Kukhareva, and L. K. Vasyanina. "Aminomethylation of dihydroquercetin." Doklady Chemistry 448, no. 1 (2013): 4–8. http://dx.doi.org/10.1134/s0012500813010011.

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7

Kunitskaya, Larisa, Tatyata Zheltonozhskaya, and Tatyana Rechun. "Polymer-Analogous Transformations in Triblock Copolymers Containing Polyacrylamide and Poly(ethylene oxide)." French-Ukrainian Journal of Chemistry 3, no. 2 (2015): 140–45. http://dx.doi.org/10.17721/fujcv3i2p140-145.

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The polymer-analogous conversion of triblock copolymers (TBC) PAAm-b-PEO-b-PAAm by the aminomethylation reaction in PAAm blocks under the effect of dimethylamine and formaldehyde (Mannich’s reaction) was studied. Kinetic investigations of the Mannich’s reaction in TBC as compared to that in pure PAAm were performed by potentiometric titration. The existence of two competitive polymer-analogous transformations in PAAm chains of all the (co)polymers such as aminomethylation and alkaline hydrolysis of amide groups was established and discussed.

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8

Fujii, Shintaro, Takehito Konishi, Yusuke Matsumoto, Yousuke Yamaoka, Kiyosei Takasu, and Ken-ichi Yamada. "Radical Aminomethylation of Imines." Journal of Organic Chemistry 79, no. 17 (2014): 8128–33. http://dx.doi.org/10.1021/jo501332j.

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9

Luostarinen, Minna, Alexander Shivanyuk, and Kari Rissanen. "Partial Aminomethylation of Resorcarenes." Organic Letters 3, no. 26 (2001): 4141–44. http://dx.doi.org/10.1021/ol016658e.

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10

Yusubov, N. N. "Aminomethylation of (?-alkylthioalkyl)phenols." Russian Chemical Bulletin 45, no. 6 (1996): 1433–36. http://dx.doi.org/10.1007/bf01434227.

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11

Karavai, V. P., and P. N. Gaponik. "Aminomethylation of 1-methyltetrazole." Chemistry of Heterocyclic Compounds 21, no. 4 (1985): 474. http://dx.doi.org/10.1007/bf00504419.

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12

Nifant’ev, E. E., P. V. Slitikov, and E. N. Rasadkina. "Bis(aminomethylation) of dihydroxynaphthalenes." Doklady Chemistry 463, no. 1 (2015): 178–80. http://dx.doi.org/10.1134/s0012500815070046.

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13

Bondarenko, Svitlana P., Vera N. Ishchenko, and Mykhaylo S. Frasinyuk. "Chemoselective aminomethylation of harmol." Chemistry of Heterocyclic Compounds 54, no. 11 (2018): 1061–64. http://dx.doi.org/10.1007/s10593-018-2392-x.

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14

Gao, Fan, Deng Tao, Cheng Ju, et al. "Regioselectivity of aminomethylation in 3-acetyl-7-hydroxycoumarins: Mannich bases and Betti bases." New Journal of Chemistry 45, no. 22 (2021): 9864–71. http://dx.doi.org/10.1039/d1nj01584b.

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15

Li, Jianxia, Jieqiong Dong, Jie Ouyang, et al. "Synthesis, characterization, solubilization, cytotoxicity and antioxidant activity of aminomethylated dihydroquercetin." MedChemComm 8, no. 2 (2017): 353–63. http://dx.doi.org/10.1039/c6md00496b.

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16

Li, Song, Qi-Chao Shan, Lu-Min Hu, Xue-Qing Ma, and Xu-Hong Hu. "Merging alkenyl C–H activation with the ring-opening of 1,2-oxazetidines: ruthenium-catalyzed aminomethylation of enamides." Chemical Communications 56, no. 57 (2020): 7969–72. http://dx.doi.org/10.1039/d0cc03081c.

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17

Meng, Xiu-Jin, Yong-Zhou Pan, Shi-Kun Mo, Heng-Shan Wang, Hai-Tao Tang та Ying-Ming Pan. "Electrochemical α-methoxymethylation and aminomethylation of propiophenones using methanol as a green C1 source". Organic Chemistry Frontiers 7, № 17 (2020): 2399–404. http://dx.doi.org/10.1039/d0qo00593b.

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18

R., S. Varma. "Aminomethylation reactions of nitrogen and sulfur five membered heterocyclic compounds." Journal of India Chemical Society Vol 81, Aug 2004 (2004): 627–38. https://doi.org/10.5281/zenodo.5829941.

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Department of Chemistry, University of Lucknow, Lucknow-226 007, India <em>E-mail : </em>profraj @sancharnet.in Five membered nitrogen and sulfur heterocyclic compounds such as isatins, benzimidazole, benzimidazolin-2-thione, benzoxazoli none- 2, benzoxazoline-2-thione, benzotriazole, benzothiazoline-2 -thione, 1 ,3,4-oxadiazoline-5-thione and 1,2,4-triazolin-5-thiones have been prepared and subjected to aminomethylation reactions in presence of formaldehyde and amines. Secondary as well as primary aromatic amines bearing different substituents have been successfully utilized in the aminomethy

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19

Ibragimov, A. G., M. G. Shaibakova, L. K. Dilmukhametova, E. A. Paramonov, Yu Yu Mayakova, and I. R. Ramazanov. "CATALYTIC AMINOMETHYLATION OF PHENOLS USING Cu(I)-BASED CATALYSTS IMMOBILIZED ON SILICA GEL." Izvestia Ufimskogo Nauchnogo Tsentra RAN, no. 2 (June 16, 2025): 26–30. https://doi.org/10.31040/2222-8349-2025-0-2-26-30.

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The article is devoted to the study of aminomethylation of phenols using new effective catalysts, which opens up prospects for obtaining aminomethylated derivatives with high activity and a wide range of applications. The authors' group headed by Doctor of Chemical Sciences A.G. Ibragimov refers to a previously developed method that uses N,N,N',N'-tetramethylmethanediamine (bisamine) as a reagent for aminomethylation of alkynes in combination with various catalysts based on transition metals such as Cu, V, Sm, which allows achieving high yields of final products. This article discusses in deta

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20

Slitikov, P. V., and Yu B. Evdokimenkova. "Aminomethylated Hydroxinaphthalenes: Synthesis and Application." Herald of the Bauman Moscow State Technical University. Series Natural Sciences, no. 1 (94) (February 2021): 126–43. http://dx.doi.org/10.18698/1812-3368-2021-1-126-143.

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The analysis of the literature is carried out and the results of the synthetic approaches to the aminomethylation of hydroxy derivatives of naphthalenes developed over the past 20 years are presented. Most of the described aminomethylation processes proceed as Mannich aminomethylation or, as a special case of a similar condensation --- aminobenzylation according to Betti. The results of all studies are grouped according to the nature of the amine used in the synthesis: primary, secondary, tertiary. Most of the examples were considered for 2-naphthol, however, as the analysis of literature data

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21

Gevorkyan, A. A., A. S. Arakelyan, A. A. Movsisyan, Zh L. Dzhandzulyan, and K. A. Petrosyan. "Improved procedure of acetylene aminomethylation." Russian Journal of General Chemistry 76, no. 7 (2006): 1175. http://dx.doi.org/10.1134/s1070363206070310.

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22

Quiclet-Sire, Béatrice, and Samir Z. Zard. "Radical Aminomethylation of Unactivated Alkenes." Organic Letters 10, no. 15 (2008): 3279–82. http://dx.doi.org/10.1021/ol801162m.

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23

Gellman, S., and Y. Chi. "Enantioselective Organocatalytic Aminomethylation of Aldehydes." Synfacts 2006, no. 7 (2006): 0724. http://dx.doi.org/10.1055/s-2006-941908.

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24

Mondal, Susmita, Sadhanendu Samanta, Mukta Singsardar, and Alakananda Hajra. "Aminomethylation of Imidazoheterocycles with Morpholine." Organic Letters 19, no. 14 (2017): 3751–54. http://dx.doi.org/10.1021/acs.orglett.7b01594.

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25

Karavai, V. P., and P. N. Gaponik. "Aminomethylation of 1-R-Tetrazoles." Chemistry of Heterocyclic Compounds 27, no. 1 (1991): 55–60. http://dx.doi.org/10.1007/bf00633218.

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26

MOEHRLE, H., M. PYCIOR, and J. LESSEL. "ChemInform Abstract: Aminomethylation of Picolines." ChemInform 28, no. 18 (2010): no. http://dx.doi.org/10.1002/chin.199718171.

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27

Krivonogov, V. P., G. A. Tolstikov, Yu I. Murinov, et al. "ChemInform Abstract: Aminomethylation of Pyrimidines." ChemInform 32, no. 29 (2010): no. http://dx.doi.org/10.1002/chin.200129155.

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28

Smirnov, L. D., Yu V. Kuznetsov, L. G. Stolyarova, and V. P. Lezina. "Aminomethylation of 5(6)-hydroxybenzimidazole." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 8 (1985): 1705–8. http://dx.doi.org/10.1007/bf00948521.

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29

Smirnova, A. A., and E. V. Tret’yakova. "Chemoselective aminomethylation of quinopimaric acid." Russian Chemical Bulletin 72, no. 10 (2023): 2404–10. http://dx.doi.org/10.1007/s11172-023-4040-6.

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30

Patel, Om P. S., Nitesh Kumar Nandwana, Ajay Kumar Sah, and Anil Kumar. "Metal-free synthesis of aminomethylated imidazoheterocycles: dual role of tert-butyl hydroperoxide as both an oxidant and a methylene source." Organic & Biomolecular Chemistry 16, no. 44 (2018): 8620–28. http://dx.doi.org/10.1039/c8ob02432d.

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31

Ghosh, Payel, Sadhanendu Samanta, Sumit Ghosh, Sourav Jana, and Alakananda Hajra. "Aminomethylation of imidazopyridines using N,N-dimethylformamide as an aminomethylating reagent under Cu(II)-catalysis." Tetrahedron Letters 61, no. 49 (2020): 152581. http://dx.doi.org/10.1016/j.tetlet.2020.152581.

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32

Gupta, Sonu, Nisha Chandna, Pooja Dubey, Ajai K. Singh, and Nidhi Jain. "GO–Cu7S4 catalyzed ortho-aminomethylation of phenol derivatives with N,N-dimethylbenzylamines: site-selective oxidative CDC." Chemical Communications 54, no. 54 (2018): 7511–14. http://dx.doi.org/10.1039/c8cc03396j.

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33

Frasinyuk, Mykhaylo S., Svitlana P. Bondarenko, Volodymyr P. Khilya, Chunming Liu, David S. Watt, and Vitaliy M. Sviripa. "Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals." Organic & Biomolecular Chemistry 13, no. 4 (2015): 1053–67. http://dx.doi.org/10.1039/c4ob02137a.

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34

Xu, Ji-Hang, Zi-Kui Liu, Yan-Liu Tang, Yang Gao, and Xiao-Qiang Hu. "Merging strain-release and copper catalysis: the selective ring-opening cross-coupling of 1,2-oxazetidines with boronic acids." Chemical Communications 58, no. 26 (2022): 4180–83. http://dx.doi.org/10.1039/d2cc00461e.

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A facile copper catalysed ring-opening cross-coupling of highly strained 1,2-oxazetidines with arylboronic acids has been achieved for the first time, delivering a wide range of aminomethylation products in useful to good yields.

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35

Talybov, G. M. "Enantioselective aminomethylation of 1-(benzyloxy)propan-2-one with an aromatic C-ethyl substituted propargyl amine ether." Журнал органической химии 59, no. 6 (2023): 815–18. http://dx.doi.org/10.31857/s0514749223060113.

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Enantioselective aminomethylation of 1-(benzyloxy)propan-2-one with an aromatic propargyl amino ether in the presence of a chiral pseudoephedrine catalyst in an aqueous medium gave anti / syn products with high yields and optical purity.

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36

Shokol, Tetyana, Anastasiya Suprun, Viktoriia Moskvina, and Volodymyr Khilya. "Hetarenocoumarins based on 7-hydroxy-3-(benzothiazol-2-yl)coumarin." French-Ukrainian Journal of Chemistry 9, no. 2 (2021): 83–93. http://dx.doi.org/10.17721/fujcv9i2p83-93.

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The syntheses of angular hetarenocoumarins, namely chromeno[8,7-e][1,3]oxazin-2-ones and furo[2,3-h]chromen-2-one, have been accomplished starting from 7-hydroxy-3-(benzothiazol-2-yl)-coumarin using aminomethylation and formylation reactions.

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37

Córdova, Armando, Ismail Ibrahem та Pawel Dziedzic. "Organocatalytic Asymmetric α-Aminomethylation of Cyclohexanones". Synthesis 2006, № 23 (2006): 4060–64. http://dx.doi.org/10.1055/s-2006-950346.

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38

Khrustalev, D. P., G. T. Khamzina, S. D. Fazylov, and A. M. Gazaliev. "Aminomethylation of phenylacetylene under microwave irradiation." Russian Journal of General Chemistry 77, no. 5 (2007): 970. http://dx.doi.org/10.1134/s1070363207050301.

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39

Bieber, L., I. Estevam, and M. da Silva. "Zinc-Promoted Aminomethylation of Organic Halides." Synfacts 2006, no. 01 (2005): 0061. http://dx.doi.org/10.1055/s-2005-921729.

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40

Schaffrath, Heike, and Wilhelm Keim. "Regio control in ruthenium catalysed aminomethylation." Journal of Molecular Catalysis A: Chemical 140, no. 2 (1999): 107–13. http://dx.doi.org/10.1016/s1381-1169(98)00230-1.

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41

Schulte, M. M., J. Herwig, R. W. Fischer, and C. W. Kohlpaintner. "Amine synthesis via carbonylation reactions: aminomethylation." Journal of Molecular Catalysis A: Chemical 150, no. 1-2 (1999): 147–53. http://dx.doi.org/10.1016/s1381-1169(99)00222-8.

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42

Bondarenko, S. P., M. S. Frasinyuk, and V. P. Khilya. "Aminomethylation of 3-aryl-7-hydroxycoumarins." Chemistry of Heterocyclic Compounds 46, no. 5 (2010): 529–35. http://dx.doi.org/10.1007/s10593-010-0541-y.

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43

Baranova, Yu B., and A. N. Gafarov. "Sulfo- and aminomethylation of 4-isononylphenol." Russian Journal of Applied Chemistry 82, no. 10 (2009): 1780–84. http://dx.doi.org/10.1134/s1070427209100061.

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44

Shustov, Gennady, and Vladimir Khlebnikov. "Aminomethylation of BINOL with methyleneiminium salts." Canadian Journal of Chemistry 89, no. 11 (2011): 1319–24. http://dx.doi.org/10.1139/v11-100.

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A new method for synthesizing chiral 3,3′-bis(N,N-dialkylaminomethyl)-1,1′-bi-2-naphthols with high enantiomeric excess is described. The procedure consists of bis-lithiation of diprotected (S)- or (R)-1,1′-bis(2-naphthol) followed by treatment of the intermediate with methyleneiminium salts. Mild reaction conditions prevent racemization and provide 3,3′-bis(N,N-dialkylaminomethyl)-1,1′-bi-2-naphthols or 3-(N,N-dialkylaminomethyl)-1,1′-bi-2-naphthols with an enantiomeric excess >99%.

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45

Kalinin, A. V., �. T. Apasov, S. L. Ioffe, V. P. Kozyukov, and Vik P. Kozyukov. "Nonaqueous aminomethylation of silylated polynitrogen heterocycles." Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 34, no. 6 (1985): 1325–27. http://dx.doi.org/10.1007/bf00956120.

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46

Varlamov, S. V., G. K. Kadorkina, and R. G. Kostyanovskii. "Hydroxy-, alkoxy-, aminomethylation of NH-oxaziridines." Chemistry of Heterocyclic Compounds 24, no. 3 (1988): 320–25. http://dx.doi.org/10.1007/bf00475333.

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47

Fujii, Shintaro, Takehito Konishi, Yusuke Matsumoto, Yousuke Yamaoka, Kiyosei Takasu, and Ken-ichi Yamada. "ChemInform Abstract: Radical Aminomethylation of Imines." ChemInform 46, no. 10 (2015): no. http://dx.doi.org/10.1002/chin.201510077.

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48

PRISHCHENKO, A. A., M. V. LIVANTSOV, D. A. PISARNITSKII, and V. S. PETROSYAN. "ChemInform Abstract: Aminomethylation of Diethyl Pivaloylphosphonite." ChemInform 24, no. 6 (2010): no. http://dx.doi.org/10.1002/chin.199306228.

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49

Fujiwara, Yuzo, and Chengguo Jia. "New developments in transition metal-catalyzed synthetic reactions via C-H bond activation." Pure and Applied Chemistry 73, no. 2 (2001): 319–24. http://dx.doi.org/10.1351/pac200173020319.

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Several novel and useful reactions involving transition metal-catalyzed C-H bond activation discovered in our laboratory have been summarized here, which includes olefin arylation, hydroarylation of alkynes, carboxylation of arenes and alkanes, and acetoxylation and aminomethylation of alkanes. Possible mechanisms of these reactions have been suggested.

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50

Holla, Bantwala S., Channamata S. Prasanna, Boja Poojary, Mithun Ashok, Kottapalli S. Rao, and Kanakamajalu Shridhara. "Synthesis, Characterization and Antibacterial Studies of Some 1,2,4-Triazole Derivatives Containing a 6-Chloropyridin-3-yl methyl Moiety." Zeitschrift für Naturforschung B 61, no. 3 (2006): 334–38. http://dx.doi.org/10.1515/znb-2006-0315.

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Abstract5-(6-Chloropyridin-3-yl methyl)-4-phenyl-1,2,4-triazole-3-thiol (2) and 5-substituted-4-phenyl- 1,2,4-triazole-3-thiols (3) were synthesized. Alkylation and aminomethylation reactions of these triazoles were also carried out. Some of the newly synthesized compounds were screened for their antibacterial activities.

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