3558-62-1Relevant academic research and scientific papers
Synthesis of Poly-Substituted Pyridines via Noble-Metal-Free Cycloaddition of Ketones and Imines
Mao, Yeting,Mao, Hong,Xu, Jiaojiao,Liu, Tianqi,Liu, Bingxin,Tan, Qitao,Ding, Chang-Hua,Xu, Bin
supporting information, p. 3905 - 3908 (2021/10/20)
An eco-friendly and noble-metal-free formal [4+2] cycloaddition reaction was developed for the efficient synthesis of biologically interesting poly-substituted pyridines from easily available ketones and imines, whereby two sequential C?C bonds are formed. The given approach features a unique synthetic strategy of imines and ketones with wide substrate scope, good functional group tolerance, mild conditions and operational simplicity, which represents a more direct pathway to synthesize poly-substituted pyridines than traditional methods.
Regiocontrolled synthesis of 2,4,6-triarylpyridines from methyl ketones, electron-deficient acetylenes and ammonium acetate
Shabalin, Dmitrii A.,Dvorko, Marina Yu.,Schmidt, Elena Yu.,Trofimov, Boris A.
supporting information, p. 2703 - 2715 (2021/04/07)
A novel one-pot two-step approach for the synthesis of 2,4,6-triarylpyridinesvia t-BuOK/DMSO-promotedC-vinylation of a variety of methyl ketones with electron-deficient acetylenes (alkynones) followed by a cyclization of thein situgenerated unsaturated 1,5-dicarbonyl species with ammonium acetate has been developed. This approach possesses competitive advantages such as high regioselectivity, available starting materials and the absence of transition-metal catalysts, oxidants and undesirable byproducts. A wide synthetic utility of the developed approach was demonstrated by the synthesis of trisubstituted, tetrasubstituted and fused pyridines.
Method for synthesizing polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under catalysis of ferric salt
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Paragraph 0094-0097, (2020/06/02)
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for synthesizing a polysubstituted pyridine derivative based on oxime ester and unsaturated ketone under the catalysis of ferric salt. For the first ti
Selective Dehydrogenative Acylation of Enamides with Aldehydes Leading to Valuable β-Ketoenamides
Liu, Rui-Hua,Shen, Zhen-Yao,Wang, Cong,Loh, Teck-Peng,Hu, Xu-Hong
, p. 944 - 949 (2020/02/15)
We have presented a unique example of dehydrogenative acylation of enamides with aldehydes enabled by an earth-abundant iron catalyst. The protocol provides the straightforward access to valuable β-ketoenamides with ample substrate scope and excellent functional group tolerance. Notably, distinct C-H acylation of enamide rather than at N-H moiety site occurs with absolute Z-selectivity was observed. Late-stage modifications of complex molecules and versatile synthetic utility of β-ketoenamides further highlight the practicability of this transformation.
Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines
Tan, Wei Wen,Ong, Yew Jin,Yoshikai, Naohiko
supporting information, p. 8240 - 8244 (2017/06/30)
A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.
Highly functionalized pyridines synthesis from N-sulfonyl ketimines and alkynes using the N-S bond as an internal oxidant
Zhang, Qian-Ru,Huang, Ji-Rong,Zhang, Wei,Dong, Lin
, p. 1684 - 1687 (2014/04/17)
The N-S bond-based internal oxidant offers a distinct approach for the synthesis of highly functionalized pyridines. A novel Rh(III)-catalyzed one-pot process undergoes an efficient C-C/C-N bond formation along with desulfonylation under very mild conditions. The method is quite simple, general, and efficient.
Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage
Yamamoto, Shun-Ichi,Okamoto, Kana,Murakoso, Makiko,Kuninobu, Yoichiro,Takai, Kazuhiko
supporting information; experimental part, p. 3182 - 3185 (2012/07/28)
A new method is described for the regioselective synthesis of multisubstituted pyridine derivatives. Treatment of N-acetyl β-enamino ketones with alkynes in the presence of the rhenium catalyst, Re 2(CO)10, gives multisubstituted pyridines regioselectively. In this reaction, the N-acetyl moieties are important for the selective formation of the multisubstituted pyridines. This reaction proceeds via insertion of alkynes into a carbon-carbon single bond of β-enamino ketones, intramolecular nucleophilic cyclization, and elimination of acetic acid.
Pyrylium Compounds. 30. C-Alkylation of 1,3,5-Triaryl-pentene-1,5-dione Enolates: A Simple Approach to 3-Alkylsubstituted 2,4,6-Triarylpyrylium Salts
Fischer, Gerhard W.
, p. 983 - 997 (2007/10/02)
1,3,5-Triaryl-pentene-1,5-dione enolates (10), obtainable in crystalline form from 2,4,6-triarylpyrylium pseudobases (9) and sodium methoxide in benzene/ether, react in dipolar aprotonic solvents (e.g.DMSO, DMF) with various types of alkyl iodides to give
Pyrylium Compounds. XXIII. 2-Dialkylamino-2H-pyrans from Tetra- and Pentasubstituted Pyrylium Salts
Fischer, Gerhard W.,Zimmermann, Thomas,Weissenfels, Manfred
, p. 657 - 666 (2007/10/02)
Tetra- and pentasubstituted pyrylium salts of type 6 react with secondary alkyl amines to give stable crystalline 2-dialkylamino-2H-pyrans 7.In the case of tetrasubsituted pyrylium salts 6, R' = Me, R'' = H the reaction occurs regioselectively leading to 2H-pyrans with Me at C-3 of the heterocyclic ring.The structure of the reaction products was established by n.m.r., i.r., u.v. and mass spectroscopic methods.Electrophilic agents like protons, carboxylic acid chlorides or methyl iodide regenerate the original pyrylium cations from 7.In refluxing methanol 7a is converted into the 2-methoxy-2H-pyran derivative 8, whereas in aqueous acetone the pseudobase 9 and with ammonia the pyridine 10 are formed.Reaction of 7a with nitromethane or ethyl cyanoacetate provides the benzene derivatives 11 and 12, respectively.
