Cargando…

Triethylamine-Promoted Oxidative Cyclodimerization of 2H-Azirine-2-carboxylates to Pyrimidine-4,6-dicarboxylates: Experimental and DFT Study

An unprecedented oxidative cyclodimerization reaction of 2H-azirine-2-carboxylates to pyrimidine-4,6-dicarboxylates under heating with triethylamine in air is described. In this reaction, one azirine molecule undergoes formal cleavage across the C-C bond and another across the C=N bond. According to...

Descripción completa

Detalles Bibliográficos
Autores principales:	Zakharov, Timofei N., Sakharov, Pavel A., Novikov, Mikhail S., Khlebnikov, Alexander F., Rostovskii, Nikolai V.
Formato:	Online Artículo Texto
Lenguaje:	English
Publicado:	MDPI 2023
Materias:	Article
Acceso en línea:	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254727/ https://www.ncbi.nlm.nih.gov/pubmed/37298789 http://dx.doi.org/10.3390/molecules28114315

Ejemplares similares

Non-natural 2H-azirine-2-carboxylic acids: an expedient synthesis and antimicrobial activity
por: Sakharov, Pavel A., et al.
Publicado: (2019)

Copper(II)-Catalyzed (3+2) Cycloaddition of 2H-Azirines to Six-Membered Cyclic Enols as a Route to Pyrrolo[3,2-c]quinolone, Chromeno[3,4-b]pyrrole, and Naphtho[1,8-ef]indole Scaffolds
por: Sakharov, Pavel A., et al.
Publicado: (2022)

Azirinium ylides from α-diazoketones and 2H-azirines on the route to 2H-1,4-oxazines: three-membered ring opening vs 1,5-cyclization
por: Rostovskii, Nikolai V, et al.
Publicado: (2015)

5-Chloroisoxazoles: A Versatile Starting Material for the Preparation of Amides, Anhydrides, Esters, and Thioesters of 2H-Azirine-2-carboxylic Acids
por: Agafonova, Anastasiya V., et al.
Publicado: (2022)

Isomerization of 5-(2H-Azirin-2-yl)oxazoles: An Atom-Economic Approach to 4H-Pyrrolo[2,3-d]oxazoles
por: Zanakhov, Timur O., et al.
Publicado: (2021)

Domino reactions of 2H-azirines with acylketenes from furan-2,3-diones: Competition between the formation of ortho-fused and bridged heterocyclic systems
por: Khlebnikov, Alexander F, et al.
Publicado: (2014)

Blue Light-Promoted Cross-Coupling of α-Diazo Esters with Isocyanides: Synthesis of Ester-Functionalized Ketenimines
por: Sakharov, Pavel A., et al.
Publicado: (2022)

Electrochemical Iodine‐Mediated Oxidation of Enamino‐Esters to 2H‐Azirine‐2‐Carboxylates Supported by Design of Experiments
por: Babaoglu, Emre, et al.
Publicado: (2020)

Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination
por: Sun, Jiyun, et al.
Publicado: (2018)

6-Benzyl 4-ethyl 2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-4,6-dicarboxylate
por: Guo, Huan-Mei
Publicado: (2011)

Tetraaqua(pyrimidine-4,6-dicarboxylato-κ(2) N (1),O (6))magnesium monohydrate
por: Starosta, Wojciech, et al.
Publicado: (2013)

Poly[[hexaaquabis(μ(3)-pyrimidine-4,6-dicarboxylato)dicalcium] dihydrate]
por: Starosta, Wojciech, et al.
Publicado: (2012)

Poly[hexaaquabis(μ(4)-pyrimidine-4,6-dicarboxylato)tetralithium]
por: Starosta, Wojciech, et al.
Publicado: (2012)

Benzil/triethylamine: a photo-reducing system for Cu(2+)
por: Schmallegger, Max, et al.
Publicado: (2018)

2-Iodo-4,6-dimethylpyrimidine
por: Jiang, Qing-Min, et al.
Publicado: (2010)

4,6-Dimethylpyrimidin-2-amine
por: Fu, Wei-Wei, et al.
Publicado: (2012)

Supramolecular-induced regiocontrol over the photochemical [4 + 4] cyclodimerization of NHC- or azole-substituted anthracenes
por: Bai, Sha, et al.
Publicado: (2020)

Addition and Cycloaddition Reactions of Phosphinyl- and Phosphonyl-2H-Azirines, Nitrosoalkenes and Azoalkenes
por: Lemos, Américo
Publicado: (2009)

4,6-Dimethyl-2-p-tolylpyrimidine
por: Xu, Chen, et al.
Publicado: (2009)

Ethyl 2-(2,6-difluorobenzyloxy)-4-(4,6-dimethoxypyrimidin-2-yl)quinoline-3-carboxylate
por: Li, Yuan-xiang
Publicado: (2009)

N-Butyl-4,6-diphenylpyrimidin-2-amine
por: Fun, Hoong-Kun, et al.
Publicado: (2011)

4,6-Dimethyl-2-(naphthalen-1-yl)pyrimidine
por: Zhang, Xiao-Xue, et al.
Publicado: (2011)

Probing the Structural and Electronic Effects on the Origin of π-Facial Stereoselectivity in 1-Methylphosphole 1-Oxide Cycloadditions and Cyclodimerization
por: Bhai, Surjit, et al.
Publicado: (2018)

Dimethyl 2-aminobiphenyl-4,4′-dicarboxylate
por: Lehane, Ryan L., et al.
Publicado: (2013)

Dimethyl 2-nitrobiphenyl-4,4′-dicarboxylate
por: Vieira, Vanessa C. M., et al.
Publicado: (2014)

Bis[2-((4,6-dimethylpyrimidin-2-yl){2-[(4,6-dimethylpyrimidin-2-yl)sulfanyl]ethyl}amino)ethyl] disulfide
por: Wang, Guo-Qing, et al.
Publicado: (2010)

2-[(4,6-Dimethoxypyrimidin-2-yl)oxy]benzaldehyde
por: He, Xue-Jun, et al.
Publicado: (2012)

Di-μ-bromido-bis({2-[(4,6-dimethylpyrimidin-2-yl)disulfanyl]-4,6-dimethylpyrimidine-κ(2) N (1),S (2)}copper(I))
por: Nimthong, Ruthairat, et al.
Publicado: (2012)

1-(4,6-Dimethylpyrimidin-2-yl)thiourea
por: Saeed, Sohail, et al.
Publicado: (2011)

4,6-Dimethoxy-2-(methylsulfanyl)pyrimidine
por: Balasubramani, Kasthuri, et al.
Publicado: (2009)

2-Methyl-4,6-bis(1-methylhydrazino)pyrimidine
por: Hutchinson, Daniel J., et al.
Publicado: (2009)

4,6-Dimethoxy-2-(methylsulfonyl)pyrimidine
por: Fun, Hoong-Kun, et al.
Publicado: (2010)

2-Amino-4,6-dimethylpyrimidin-1-ium chloride
por: Hu, Hui-Ling, et al.
Publicado: (2012)

Hydrothermal Synthesis of CeO(2)-SnO(2) Nanoflowers for Improving Triethylamine Gas Sensing Property
por: Xue, Dongping, et al.
Publicado: (2018)

Dimethyl 2,2′-dinitrobiphenyl-4,4′-dicarboxylate
por: Lehane, Ryan L., et al.
Publicado: (2014)

DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C–N cross-coupling and the origin of ring-opening of 2H-azirines
por: Yu, Fan, et al.
Publicado: (2021)

Bis(μ(3)-pyrimidine-4-carboxylato)bis(μ(2)-pyrimidine-4-carboxylato)tetrakis(aqualithium)
por: Starosta, Wojciech, et al.
Publicado: (2012)

Copper(I)-catalyzed asymmetric decarboxylative Mannich reaction enabled by acidic activation of 2H-azirines
por: Zhang, Hai-Jun, et al.
Publicado: (2019)

A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines
por: Zhang, Guangtao, et al.
Publicado: (2019)

4,6-Dichloro-5-methoxypyrimidine
por: Fun, Hoong-Kun, et al.
Publicado: (2010)

Cannot write session to /tmp/vufind_sessions/sess_af4nltsubqmqlt2o5pgs1ut2u7