- Method for preparing 2-amino-4-methyl-1-propyl-1H-pyrrole-3-carbonitrile
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The invention discloses a method for preparing 2-amino-4-methyl-1-propyl-1H-pyrrole-3-carbonitrile, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: taking epoxypropane and n-propylamine as raw materials; after hydrogen on a nitrogen atom is protected, oxidizing, removing a protecting group, and cyclizing with malononitrile to obtain the 2-amino-4-methyl-1-propyl-1H-pyrrole-3-carbonitrile. The method has the advantages of high product yield, high purity, accessible raw materials and simple operation, and is beneficial to industrialproduction.
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Paragraph 0034-0036; 0041; 0042; 0047; 0048
(2021/01/28)
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- Platinum-Catalyzed, Terminal-Selective C(sp3)-H Oxidation of Aliphatic Amines
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This Communication describes the terminal-selective, Pt-catalyzed C(sp3)-H oxidation of aliphatic amines without the requirement for directing groups. CuCl2 is employed as a stoichiometric oxidant, and the reactions proceed in high yield at Pt loadings as low as 1 mol%. These transformations are conducted in the presence of sulfuric acid, which reacts with the amine substrates in situ to form ammonium salts. We propose that protonation of the amine serves at least three important roles: (i) it renders the substrates soluble in the aqueous reaction medium; (ii) it limits binding of the amine nitrogen to Pt or Cu; and (iii) it electronically deactivates the C-H bonds proximal to the nitrogen center. We demonstrate that this strategy is effective for the terminal-selective C(sp3)-H oxidation of a variety of primary, secondary, and tertiary amines.
- Lee, Melissa,Sanford, Melanie S.
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supporting information
p. 12796 - 12799
(2015/10/28)
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- Syntheses of five- and seven-membered ring sultam derivatives by Michael addition and Baylis-Hillman reactions
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Five- and seven-membered sultam derivatives were conveniently synthesized via intra- or intermolecular Michael additions and an improved vinyl sulfonamide Baylis-Hillman reaction. Two different cyclization pathways were explored for the oxa-Michael reaction. A good solvent was discovered for an otherwise sluggish ketone-type Baylis-Hillman reaction in which vinyl sulfonamide ketones were used as the precursors. Furthermore, a strong base caused vinyl sulfonamide ketones to undergo 5-endo-trig intramolecular cyclizations, which are disfavored according to Baldwin's rule. Finally Baylis-Hillman reaction products were used as scaffolds for diversity-oriented sultam syntheses.
- Tong, Kun,Tu, Jinchang,Qi, Xueyong,Wang, Min,Wang, Yanjie,Fu, Haizhen,Pittman Jr., Charles U.,Zhou, Aihua
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supporting information
p. 2369 - 2375
(2013/03/29)
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