- 3-Substituted 2-isocyanopyridines as versatile convertible isocyanides for peptidomimetic design
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We report the use of 3-substituted 2-isocyanopyridines as convertible isocyanides in Ugi four-component reactions. TheN-(3-substituted pyridin-2-yl)amide Ugi products can be cleaved by amines, alcohols, and water with Zn(OAc)2as a catalyst. In addition, the applicability of the method was demonstrated in constrained di-/tripeptides bearing acid and base sensitive protective groups obtainedviaUgi-4CR post-condensation modifications.
- Ballet, Steven,Elsocht, Mathias,Hollanders, Charlie,Jida, Mouhamad,Maes, Bert U. W.,Renders, Evelien,Van der Poorten, Olivier
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p. 6863 - 6866
(2021/07/19)
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- Selectfluor-promoted regioselective chlorination/bromination of 2-aminopyridines and 2-aminodiazines using LiCl/LiBr
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Using LiCl as a chlorine source, the chlorination of 2-aminopyridines or 2-aminodiazines in the presence of Selectfluor and DMF is established under mild conditions. This method gives chlorinated pyridines or diazines in good to high yields with high regioselectivities. Also, this method is extended to the bromination of 2-aminopyridines or 2-aminodiazines by using LiBr. The regioselectivity of the chlorination reaction is strongly dependent upon the substituent pattern in either the 2-aminopyridines or 2-aminodiazines. The synthesis of Buparlisib from chlorinated pyridines was explored. A study of the mechanism revealed that this chlorination occurs via either a pyridine or diazine radical process.
- Hu, Jiao,Zhou, Gang,Tian, Yawei,Zhao, Xiaoming
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supporting information
p. 6342 - 6345
(2019/07/10)
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- Preparation method of 2-amino substituted six-membered nitrogen-containing heterocycle complex
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The invention discloses a preparation method of a 2-amino substituted six-membered nitrogen-containing heterocycle complex. The preparation method comprises the following steps: mix 2-fluorine substituted six-membered nitrogen-containing heterocycle complex and amidine hydrochloride salt compound, and then react under the action of a alkaline substance to obtain a 2-amino substituted six-memberednitrogen-containing heterocycle complex. Preferably, the 2-amino substituted six-membered nitrogen-containing heterocycle complex is a 2-amino pyridine compound, a 2-aminopyrimidine compound or a 2-aminopyrazine compound. Compared with the prior art, the method has the advantages of simple synthesis conditions, less reaction steps, mild reaction conditions, low cost of the catalyst used, less waste discharge and good functional group tolerance.
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Paragraph 0067; 0068
(2019/02/08)
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- Transition-metal-free access to 2-aminopyridine derivatives from 2-fluoropyridine and acetamidine hydrochloride
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Under catalyst-free conditions, an efficient method for the synthesis of 2-aminopyridine derivatives through the nucleophilic substitution and hydrolysis of 2-fluoropyridine and acetamidine hydrochloride has been developed. This amination uses inexpensive acetamidine hydrochloride as the ammonia source and has the advantages of a high yield, high chemoselectivity and wide substrate adaptability. The results suggest that other N-heterocycles containing fluorine substituents can also complete the reaction via these reaction conditions and yield the target products.
- Li, Yibiao,Huang, Shuo,Liao, Chunshu,Shao, Yan,Chen, Lu
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supporting information
p. 7564 - 7567
(2018/11/02)
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- Preparation method of intermediate 3-bromopyridine-2-amine
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The invention relates to the field of medicinal chemistry, in particular to a preparation method of a phosphatidylinositol 3-kinase inhibitor intermediate. The preparation method of 3-bromopyridine-2-amine provided by the invention includes: taking 3-bromo-5-iodopyridine-2-amine as the starting raw material, carrying out halogen-metal exchange reaction, and conducting 5-position deiodination to obtain 3-bromopyridine-2-amine. The synthesis route of 3-bromopyridine-2-amine provided by the invention is different from the existing routes, and also has high yield of the product 3-bromopyridine-2-amine, thus being suitable for industrial production.
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Paragraph 0037; 0039; 0040; 0041
(2017/03/17)
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- A quick, mild and efficient bromination using a CFBSA/KBr system
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Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.
- Jiang, Pan-Pan,Yang, Xian-Jin
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p. 90031 - 90034
(2016/10/09)
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- Fused heterotricyclic compounds as inhibitors of 17beta-hydroxysteroid dehydrogenase 3
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Fused heterotricyclic compounds, methods of using such compounds in the treatment of hormone sensitive diseases such as prostate cancer, and pharmaceutical compositions containing such compounds.
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Page/Page column 43
(2008/06/13)
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- 5,10-dihydrodipyrido[2,3-b:2,3-e]pyrazin and 5,10-dihydrodipyrido[2,3-b:3,2-e]pyrazin compounds
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A compound selected from those of formula (I): wherein: X represents N, C or CH, Y represents N when X represents C or CH, or Y represents C or CH when X represents N, R1 represents an optionally substituted alkyl, R2 and R3, which may be identical or different, represent Z or W, as defined in the description, their isomers and addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same which are useful in the treatment of cancer.
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- Novel synthetic strategy of carbolines via palladium-catalyzed amination and arylation reaction
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Four parent carbolines and the corresponding 5- or 9-methylsulfonyl derivatives were synthesized by the palladium-catalyzed intramolecular arylation reaction of ortho-bromo-substituted anilinopyridines which were prepared by the palladium-catalyzed amination reaction of iodobenzenes with aminopyridines. Carbazole and its 9-methylsulfonyl derivative were also synthesized by the same method.
- Iwaki, Takehiko,Yasuhara, Akito,Sakamoto, Takao
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p. 1505 - 1510
(2007/10/03)
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- Method for inhibition of HIV related viruses
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Treatment of AIDS, inhibition of the replication of HIV and related viruses thereof, and formulations using thiourea derivative compounds or salts thereof is disclosed. Also disclosed are novel thiourea derivative compounds.
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- TITANIUM (O) REAGENTS; 4. A SELECTIVE AND EFFICIENT REDUCTION OF NITROPYRIDINE DERIVATIVES
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Following the successful applications of a titanium (O) slurry in the deoxygenation of aromatic N-oxides, we attempted to achieve this method for the reduction of a nitro- group in pyridine derivatives.In general, only aminopyridine derivates were formed in 85-98percent yield.The advantage of this excellent reducing agent consists in mild reaction conditions and high yields of products, as well as in the selectivity of the reaction.
- Malinowski, Marek
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