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Journal articles on the topic 'Propargylic amine'

Author: Grafiati

Published: 4 June 2021

Last updated: 16 February 2022

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1

Huang, Jian, Han-Han Kong, Si-Jia Li, Rui-Jin Zhang, Hao-Dong Qian, Dan-Ran Li, Jin-Yu He, Yi-Nuo Zheng, and Hao Xu. "Asymmetric copper-catalyzed propargylic amination with amine hydrochloride salts." Chemical Communications 57, no. 38 (2021): 4674–77. http://dx.doi.org/10.1039/d1cc00663k.

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2

Fu, Rugang, and Zheng Li. "N-Propargylation of secondary amines directly using calcium carbide as an acetylene source." Journal of Chemical Research 41, no. 6 (June 2017): 341–45. http://dx.doi.org/10.3184/174751917x14949427622099.

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A one-pot N-propargylation of secondary amines has been achieved by heating the amine with formaldehyde and calcium carbide in DMSO in the presence of CuCl as a catalyst. Fifteen examples of propargylic tertiary amines, 12 of which are novel, were efficiently prepared in yields of 65–84%. The advantages of the method are broad substrate scope and a simple work-up procedure.

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3

He, Shiyu, Xufei Yan, Yanxi Lei, Haifeng Xiang, and Xiangge Zhou. "Rhodium-catalyzed annulative coupling of N-aryl-2-aminopyridine and propargylic amine via selective C–C and C–H bond activation." Chemical Communications 56, no. 15 (2020): 2284–87. http://dx.doi.org/10.1039/c9cc09777e.

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4

Yuan, Ruming, Shuhua Xu, and Gang Fu. "Mechanisms of CO2 Incorporation into Propargylic Amine Catalyzed by Ag(I)/Amine Catalysts." Journal of Organic Chemistry 83, no. 19 (September 6, 2018): 11896–904. http://dx.doi.org/10.1021/acs.joc.8b01767.

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5

Yu, Dingyi, and Yugen Zhang. "Copper-Catalyzed Three-Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines." Advanced Synthesis & Catalysis 353, no. 1 (January 10, 2011): 163–69. http://dx.doi.org/10.1002/adsc.201000691.

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6

Takeuchi, Ryo, and Ikuo Ebata. "Cationic Rhodium Complex Catalyzed Highly Selective Hydrosilylation of Propargylic Amine Derivatives." Organometallics 16, no. 16 (August 1997): 3707–10. http://dx.doi.org/10.1021/om970219v.

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7

Olivi, Nathanaël, Philippe Spruyt, Jean-François Peyrat, Mouâd Alami, and Jean-Daniel Brion. "Tandem amine propargylation-Sonogashira reactions: new three-component coupling leading to functionalized substituted propargylic amines." Tetrahedron Letters 45, no. 12 (March 2004): 2607–10. http://dx.doi.org/10.1016/j.tetlet.2004.01.141.

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8

Zeng, Suwei, Sen Xu, Yong Wang, Min Yu, Li Zhu, and Xiaoquan Yao. "Copper Nanoparticles Catalyzed Three-Component Coupling of Alkyne, Dihalomethane and Amine for the Synthesis of Propargylic Amine." Chinese Journal of Organic Chemistry 35, no. 4 (2015): 827. http://dx.doi.org/10.6023/cjoc201412045.

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9

Yu, Dingyi, and Yugen Zhang. "ChemInform Abstract: Copper-Catalyzed Three-Component Coupling of Terminal Alkyne, Dihalomethane and Amine to Propargylic Amines." ChemInform 42, no. 18 (April 7, 2011): no. http://dx.doi.org/10.1002/chin.201118051.

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10

Majumdar, Krishna C., and Gour H. Jana. "Competitive study of Meisenheimer rearrangement in a substrate tertiary amine with allylic and propargylic moieties." Canadian Journal of Chemistry 76, no. 3 (1998): 297–300. http://dx.doi.org/10.1139/cjc-76-3-297.

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11

Fujita, Ken-ichi, Akira Fujii, Junichi Sato, Shun-ya Onozawa, and Hiroyuki Yasuda. "Synthesis of 2-oxazolidinone by N-heterocyclic carbene-catalyzed carboxylative cyclization of propargylic amine with CO2." Tetrahedron Letters 57, no. 11 (March 2016): 1282–84. http://dx.doi.org/10.1016/j.tetlet.2016.02.027.

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12

Ishida, Tomonobu, Ryo Kobayashi, and Tohru Yamada. "Novel Method of Tetramic Acid Synthesis: Silver-Catalyzed Carbon Dioxide Incorporation into Propargylic Amine and Intramolecular Rearrangement." Organic Letters 16, no. 9 (April 16, 2014): 2430–33. http://dx.doi.org/10.1021/ol500806u.

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13

Matsuo, Hideaki, Jun-Chul Choi, Tadahiro Fujitani, and Ken-ichi Fujita. "Carboxylative Cyclization of a Propargylic Amine with CO₂ Catalyzed by a Silica-Coated Magnetite." Chemical and Pharmaceutical Bulletin 69, no. 7 (July 1, 2021): 698–701. http://dx.doi.org/10.1248/cpb.c21-00200.

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14

Han, Ying, and Yao-Zeng Huang. "A straightforward, efficient and versatile preparation of propargylic alcohols from 1- alkynes and aldehydes via GaI3 and amine." Tetrahedron Letters 36, no. 40 (October 1995): 7277–80. http://dx.doi.org/10.1016/0040-4039(95)01565-y.

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15

Fleming, James J., Kristin Williams Fiori, and J. Du Bois. "Novel Iminium Ion Equivalents Prepared through C−H Oxidation for the Stereocontrolled Synthesis of Functionalized Propargylic Amine Derivatives." Journal of the American Chemical Society 125, no. 8 (February 2003): 2028–29. http://dx.doi.org/10.1021/ja028916o.

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16

Cui, Jian-Fang, Karen Ka-Yan Kung, Hok-Ming Ko, Tsz-Wai Hui, and Man-Kin Wong. "ChemInform Abstract: Silver-Catalyzed Transformation of Propargylic Amine N-Oxides to Enones and Acyloxy Ketones via Isoxazolinium Intermediates." ChemInform 46, no. 13 (March 2015): no. http://dx.doi.org/10.1002/chin.201513105.

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17

Ishida, Tomonobu, Ryo Kobayashi, and Tohru Yamada. "ChemInform Abstract: Novel Method of Tetramic Acid Synthesis: Silver-Catalyzed Carbon Dioxide Incorporation into Propargylic Amine and Intramolecular Rearrangement." ChemInform 45, no. 45 (October 23, 2014): no. http://dx.doi.org/10.1002/chin.201445123.

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18

HAN, Y., and Y. Z. HUANG. "ChemInform Abstract: A Straightforward, Efficient and Versatile Preparation of Propargylic Alcohols from 1-Alkynes and Aldehydes via GaI3 and Amine." ChemInform 27, no. 3 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199603098.

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19

Majumdar, Krishna C., and Gour H. Jana. "Article." Canadian Journal of Chemistry 76, no. 3 (March 1, 1998): 297–300. http://dx.doi.org/10.1139/v98-017.

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A number of allyl aryl propargyl amines 3a-3f were synthesized in 68-82% yield. These tertiary amines were then treated with one equivalent of m-chloroperoxybenzoic acid (m-CPBA) to give products 5a-5f in 79-90% yields arising out of the Meisenheimer rearrangement of the allyl aryl amine moiety accompanying the amine oxide rearrangement of the aryl propargyl amine moiety.Key words: Meisenheimer rearrangement, [2,3] sigmatropic shift, amine oxide, propargyl amine, allyl amine.

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20

Yuan, Ruming, Baohuan Wei, and Gang Fu. "How the Coordinated Structures of Ag(I) Catalysts Affect the Outcomes of Carbon Dioxide Incorporation into Propargylic Amine: A DFT Study." Journal of Organic Chemistry 82, no. 7 (March 6, 2017): 3639–47. http://dx.doi.org/10.1021/acs.joc.7b00167.

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21

Zhou, Meng-Guang, Rui-Han Dai, and Shi-Kai Tian. "Nucleophilic addition of tertiary propargylic amines to arynes followed by a [2,3]-sigmatropic rearrangement." Chemical Communications 54, no. 47 (2018): 6036–39. http://dx.doi.org/10.1039/c8cc02176g.

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22

Obst, Martin, Akriti Srivastava, Sundarababu Baskaran, and Burkhard König. "Preparation of Propargyl Amines in a ZnCl2–Dimethylurea Deep-Eutectic Solvent." Synlett 29, no. 02 (September 21, 2017): 185–88. http://dx.doi.org/10.1055/s-0036-1588571.

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The coupling of an aldehyde, an amine, and an alkyne to yield propargyl amines was performed in a deep-eutectic solvent composed of zinc chloride and dimethylurea. The deep-eutectic solvent acts simultaneously as catalyst and solvent giving access to a variety of propargyl amines, which were isolated in moderate to very good yields.

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23

Xiao, Fuhong, Dahan Wang, Shanshan Yuan, Huawen Huang, and Guo-Jun Deng. "Iodine-promoted stereoselective amidosulfenylation of electron-deficient alkynes." RSC Advances 8, no. 41 (2018): 23319–22. http://dx.doi.org/10.1039/c8ra04374d.

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24

Yanagisawa, Akira, Toshihiko Heima, Kana Watanabe, and Shun Haeno. "Selective Propargylation of Diaryl Azo Compounds Using Metallic Barium." Synlett 31, no. 18 (August 17, 2020): 1817–22. http://dx.doi.org/10.1055/s-0040-1706414.

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The Barbier-type propargylation of azo compounds with α,γ-disubstituted propargylic tosylates was achieved by using metallic barium as the promoter. Various propargylated hydrazines (α-adducts) were exclusively synthesized from the corresponding propargylic tosylates and azobenzenes (diaryldiazenes). The thus-obtained propargylic hydrazines were further efficiently converted into propargylic amines by reductive N–N bond cleavage. Benzidine rearrangement of the propargylic hydrazines was also attempted.

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25

Shatirova, M. I. "SYNTHESIS AND PROPERTIES OF CYCLOHEXYL AMINES OF PROPARGYL SERIES." Azerbaijan Chemical Journal, no. 3 (October 2, 2020): 76–81. http://dx.doi.org/10.32737/0005-2531-2020-3-76-81.

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26

Protiva, Miroslav, Zdeněk Šedivý, Jiří Holubek, Emil Svátek, and Jiří Němec. "Cyclic amidines derived from benz[c,d]indole and 4,5-dihydro-3H-1-benzazepine including some related compounds: Synthesis and pharmacological screening." Collection of Czechoslovak Chemical Communications 50, no. 8 (1985): 1888–98. http://dx.doi.org/10.1135/cccc19851888.

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Reactions of naphthostyril (I) with primary and secondary amines and titanium tetrachloride afforded cyclic amidines III-IX. Hydrogenation of I on Pd-C resulted in the 6,7,8,8a-tetrahydro derivative X which gave by treatment with sodium amide and 3-dimethylaminopropyl chloride the N-(aminoalkyl) compound XI. Reduction of I and its N-methyl derivative II with sodium amalgam in aqueous sodium hydroxide gave the 2a,3,4,5-tetrahydro derivatives XII and XIII. Reaction of XIII with sodium amide and 3-dimethylaminopropyl chloride afforded the 2a-(aminoalkyl) compound XIV. 1,3,4,5-Tetrahydro-1-benzazepin-2-one (XV) treated with primary amines and titanium tetrachloride gave the amidines XVI-XVIII. 3-Methyl-7,8,9,9a-tetrahydro-1H-benz[d,e]isoquinoline (XIX) was reduced with sodium borohydride to compound XX which was alkylated with propargyl bromide to 1-methyl-2-propargyl-2,3,3a,4,5,6-hexahydro-1H-benz[d,e]isoquinoline (XXI). An attempt to prepare the 2-(2-phenylethyl) analogue by treatment of compound XX with phenylacetyl chloride and by the following reduction with lithium aluminium hydride resulted in the open-chain amine XXII. The lactams I, II, X, and XIII showed some discoordinating, hypothermic, peripheral vasodilating, hyperglycaemic, diuretic and antiinflammatory effects. The amidines III-IX and XVI-XVIII had local anaesthetic, slight hypotensive, antiarrhythmic, peripheral myorelaxant, papaverine-like spasmolytic and thiopental potentiating effects.

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27

Donnelly, Zhang, and Baumann. "Development of a Telescoped Flow Process for the Safe and Effective Generation of Propargylic Amines." Molecules 24, no. 20 (October 10, 2019): 3658. http://dx.doi.org/10.3390/molecules24203658.

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Propargylic amines are important multifunctional building blocks that are frequently exploited in the synthesis of privileged heterocyclic entities. Herein we report on a novel flow process that achieves the safe and effective on-demand synthesis of propargylic amines in a telescoped manner. This process minimizes exposure to hazardous azide intermediates and renders a streamlined route into these building blocks. The value of this approach is demonstrated by the rapid generation of a small selection of drug-like thiazolines that result from a high-yielding reaction cascade between propargylic amines with different aryl isothiocyanates.

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28

Yin, Guangwei, Yuanxun Zhu, Ningning Wang, Ping Lu, and Yanguang Wang. "Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: a convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones." Tetrahedron 69, no. 39 (September 2013): 8353–59. http://dx.doi.org/10.1016/j.tet.2013.07.076.

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29

Shibata, Masashi, Kazunari Nakajima, and Yoshiaki Nishibayashi. "Enantioselective intramolecular propargylic amination using chiral copper–pybox complexes as catalysts." Chem. Commun. 50, no. 58 (2014): 7874–77. http://dx.doi.org/10.1039/c4cc01676a.

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Intramolecular propargylic amination of propargylic acetates bearing an amino group at the suitable position in the presence of chiral copper–pybox complexes proceeds enantioselectively to give optically active 1-ethynyl-isoindolines (up to 98% ee).

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30

Nishibayashi, Y., G. Hattori, H. Matsuzawa, and Y. Miyake. "Enantioselective Propargylic Substitution of Propargylic Acetates with Amines." Synfacts 2008, no. 7 (July 2008): 0736. http://dx.doi.org/10.1055/s-2008-1078458.

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31

Martin, Gonzalo, Julian Ascanio, and Jesus Rodriguez. "Gas-phase thermolysis of allyl propargyl amine, allyl cyanomethyl propargyl amine, allyl propargyl 2-thiapropyl amine, and allyl methanesulfonyl propargyl amine." International Journal of Chemical Kinetics 26, no. 4 (April 1994): 487–96. http://dx.doi.org/10.1002/kin.550260409.

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32

Yin, Guangwei, Yuanxun Zhu, Ningning Wang, Ping Lu, and Yanguang Wang. "ChemInform Abstract: Lewis Acid-Promoted Cascade Reaction of Primary Amine, 2-Butynedioate, and Propargylic Alcohol: A Convenient Approach to 1,2-Dihydropyridines and 1H-Pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones." ChemInform 45, no. 6 (January 23, 2014): no. http://dx.doi.org/10.1002/chin.201406172.

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33

MARTIN, G., J. ASCANIO, and J. RODRIGUEZ. "ChemInform Abstract: Gas-Phase Thermolysis of Allyl Propargyl Amine, Allyl Cyanomethyl Propargyl Amine, Allyl Propargyl 2-Thiapropyl Amine, and Allyl Methanesulfonyl Propargyl Amine." ChemInform 25, no. 29 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199429062.

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34

Hudlicky, Tomas, Michael Moser, Scott C. Banfield, Uwe Rinner, Jean-Charles Chapuis, and George R. Pettit. "Cyclotrimerization approach to unnatural structural modifications of pancratistatin and other amaryllidaceae constituents — Synthesis and biological evaluation." Canadian Journal of Chemistry 84, no. 10 (October 1, 2006): 1313–37. http://dx.doi.org/10.1139/v06-078.

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The phenanthridone core of pancratistatin lacking all aromatic oxygenation was prepared by cyclotrimerization of acetylene-containing scaffolds 30 and 41, reflecting the natural and the C-1 epi configuration, respectively, of the amino inositol moiety. The cobalt-catalyzed formation of the aromatic core led to bisTMS derivatives 39 and 48, as well as bisacetyl derivative 51. The effectiveness of cyclotrimerization of the natural or trans series was compared with that of the cis series. In addition, the yields of cyclotrimerization were compared for propargylic amines and propargylic amides. Eleven derivatives, including the fully hydroxylated phenantridone 39, were tested against seven cancer cell lines. Three of the compounds displayed activities only an order of magnitude less than those of 7-deoxypancratistatin. Full experimental and spectral details are provided for all key compounds and future projections for the preparation of unnatural analogs of Amaryllidaceae constituents are advanced, along with some new insight into the minimum pharmacophore of pancratistatin.Key words: cyclotrimerization, alkaloids, cobalt catalyst.

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35

Sun, Renhong, Jun Liu, Shuang Yang, Ming Chen, Ning Sun, Haoyi Chen, Xin Xie, Xu You, Shi Li, and Yuanhong Liu. "Cp2TiCl2-catalyzed cis-hydroalumination of propargylic amines with Red-Al: stereoselective synthesis of Z-configured allylic amines." Chemical Communications 51, no. 29 (2015): 6426–29. http://dx.doi.org/10.1039/c5cc00950b.

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36

Marshall, James A., and Mark A. Wolf. "Amination, Aminocarbonylation, and Alkoxycarbonylation of Allenic/Propargylic Pd Intermediates Derived from Nonracemic Propargylic Mesylates: Synthesis of Nonracemic Propargyl Amines, Allenic Amides, and Butenolides." Journal of Organic Chemistry 61, no. 10 (January 1996): 3238–39. http://dx.doi.org/10.1021/jo960442m.

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37

Rezaei, Hadi, Ilan Marek, and Jean F. Normant. "Diastereoselective carbozincation of propargylic amines." Tetrahedron 57, no. 13 (March 2001): 2477–83. http://dx.doi.org/10.1016/s0040-4020(01)00069-2.

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38

Huang, Pei-Qiang, Wei Ou, and Feng Han. "Chemoselective reductive alkynylation of tertiary amides by Ir and Cu(i) bis-metal sequential catalysis." Chemical Communications 52, no. 80 (2016): 11967–70. http://dx.doi.org/10.1039/c6cc05318a.

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39

Kuang, Jinqiang, Xinjun Tang, and Shengming Ma. "Zinc diiodide-promoted synthesis of trisubstituted allenes from propargylic amines." Organic Chemistry Frontiers 2, no. 5 (2015): 470–75. http://dx.doi.org/10.1039/c5qo00047e.

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40

De Nisi, Assunta, Christian Bergamini, Marco Leonzio, Giorgio Sartor, Romana Fato, Marina Naldi, Magda Monari, Natalia Calonghi, and Marco Bandini. "Synthesis, cytotoxicity and anti-cancer activity of new alkynyl-gold(i) complexes." Dalton Transactions 45, no. 4 (2016): 1546–53. http://dx.doi.org/10.1039/c5dt02905h.

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41

MARSHALL, J. A., and M. A. WOLF. "ChemInform Abstract: Amination, Aminocarbonylation, and Alkoxycarbonylation of Allenic/ Propargylic Pd Intermediates Derived from Nonracemic Propargylic Mesylates: Synthesis of Nonracemic Propargyl Amines, Allenic Amides, and Butenolides." ChemInform 27, no. 37 (August 5, 2010): no. http://dx.doi.org/10.1002/chin.199637153.

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42

Yoshida, Akiko, Gaku Hattori, Yoshihiro Miyake, and Yoshiaki Nishibayashi. "Copper-Catalyzed Enantioselective Propargylic Amination of Nonaromatic Propargylic Esters with Amines." Organic Letters 13, no. 9 (May 6, 2011): 2460–63. http://dx.doi.org/10.1021/ol200703g.

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43

Hattori, Gaku, Hiroshi Matsuzawa, Yoshihiro Miyake, and Yoshiaki Nishibayashi. "Copper-Catalyzed Asymmetric Propargylic Substitution Reactions of Propargylic Acetates with Amines." Angewandte Chemie 120, no. 20 (May 5, 2008): 3841–43. http://dx.doi.org/10.1002/ange.200800276.

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44

Hattori, Gaku, Hiroshi Matsuzawa, Yoshihiro Miyake, and Yoshiaki Nishibayashi. "Copper-Catalyzed Asymmetric Propargylic Substitution Reactions of Propargylic Acetates with Amines." Angewandte Chemie International Edition 47, no. 20 (May 5, 2008): 3781–83. http://dx.doi.org/10.1002/anie.200800276.

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45

Hu, Jiayin, Jun Ma, Zhaofu Zhang, Qinggong Zhu, Huacong Zhou, Wenjing Lu, and Buxing Han. "A route to convert CO2: synthesis of 3,4,5-trisubstituted oxazolones." Green Chemistry 17, no. 2 (2015): 1219–25. http://dx.doi.org/10.1039/c4gc02033b.

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46

Goggiamani, Antonella, Sandro Cacchi, Giancarlo Fabrizi, Antonia Iazzetti, and Rosanna Verdiglione. "2-(Aminomethyl)-3-arylindoles from 3-(o-Trifluoroacetamidoaryl)-1-propargylic Alcohols, Aryl Halides, and Amines: A Domino Palladium-Catalyzed Three-Component Approach." Synthesis 49, no. 18 (April 28, 2017): 4163–72. http://dx.doi.org/10.1055/s-0036-1589016.

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47

Cui, Yifan, Weilong Lin, and Shengming Ma. "A metal-catalyzed new approach for α-alkynylation of cyclic amines." Chemical Science 10, no. 6 (2019): 1796–801. http://dx.doi.org/10.1039/c8sc04115f.

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48

Cacchi, Sandro, Giancarlo Fabrizi, Eleonora Filisti, Antonella Goggiamani, Antonia Iazzetti, and Loredana Maurone. "Palladium-catalyzed synthesis of 2-amino ketones from propargylic carbonates and secondary amines." Organic & Biomolecular Chemistry 10, no. 24 (2012): 4699. http://dx.doi.org/10.1039/c2ob25670c.

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49

Wang, Ji-Yu, Xu-Ling Chen, Yu Dong, Shuai He, Rui Zhang, Hua Zhang, Lei Tang, and Xiao-Mei Zhang. "A One-Pot Approach to 2-(N-Substituted Amino)-1,4-naphthoquinones with Use of Nitro Compounds and 1,4-Naphthoquinones in Water." Synlett 30, no. 05 (February 7, 2019): 615–19. http://dx.doi.org/10.1055/s-0037-1610689.

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A one-pot synthesis of 2-(N-substituted amino)-1,4-naphthoquinones from 1,4-naphthoquinones and nitro compounds in water has been developed. This method features mild reaction conditions and provides aromatic nitro compounds with various functional groups such as halogens, methylthio, ester, amide, even allyl, propargyl, and heterocycles, as well as aliphatic nitro compounds that are well tolerated. This method can be scaled up and we conducted further transformation of the obtained 2-(N-substituted amino)-1,4-naphthoquinones to synthesize carbazolequinone derivatives.

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50

Wang, Mei-Yan, Qing-Wen Song, Ran Ma, Jia-Ning Xie, and Liang-Nian He. "Efficient conversion of carbon dioxide at atmospheric pressure to 2-oxazolidinones promoted by bifunctional Cu(ii)-substituted polyoxometalate-based ionic liquids." Green Chemistry 18, no. 1 (2016): 282–87. http://dx.doi.org/10.1039/c5gc02311d.

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Cu(ii)-substituted polyoxometalate-based ionic liquids were successfully developed as halogen-free bifunctional catalysts for carboxylative cyclization of atmospheric CO₂ with propargylic amines.

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