Facile Synthesis of Substituted 4-Alkoxy-2-oxazolines and Exploration of the Reaction Mechanism

Synthesis ◽  
2016 ◽  
Vol 48 (09) ◽  
pp. 1331-1343 ◽  
Author(s):  
Bo Li ◽  
Jiye Shi ◽  
Weiliang Zhu ◽  
Jianming Zhu ◽  
Xiaolong Li ◽  
...  
Keyword(s):  
Reaction Mechanism ◽  
Facile Synthesis

Unusual Reactivity of 2,3-diphenylcyclopropenone towards N-imidoylthioureas; Facile Synthesis of 3-aryl-2,5,6-triphenylpyrimidin-4(3H)-one (PART III)

2007 ◽  
Vol 2007 (8) ◽  
pp. 439-441 ◽  
Author(s):  
Ashraf A. Aly ◽  
Ahmed M. NourEl-Din ◽  
Moshen A.-M. Gomaa ◽  
Alan B. Brown ◽  
Magda S. Fahmi
Keyword(s):  
Reaction Mechanism ◽  
Phenyl Isothiocyanate ◽  
Facile Synthesis

2,3-Diphenylcyclopropenone (1) reacts with N-imidoylthioureas 2a–e to form the pyrimidin-4(3 H)-ones 5a–e. The reaction mechanism can be described as due to stepwise addition accompanied by elimination of phenyl isothiocyanate.

Facile synthesis of quinoxaline-2-thiol and quinoxaline from α-oxo sulfines and o-aryl diamines

Synthesis ◽  
2022 ◽  
Author(s):  
Jun Dong ◽  
Youwei Chen ◽  
Xingcai Huang
Keyword(s):  
Reaction Mechanism ◽  
Nucleophilic Addition ◽  
Current Method ◽  
Facile Synthesis ◽  
Simple Strategy

A series of quinoxaline-2-thiol and quinoxaline were prepared in moderate to good yields from various phenacyl sulfoxides bearing 1-methyl-1H-tetrazole and o-aryl diamines. The proposed reaction mechanism involves generation of sulfines from the phenacyl sulfoxides bearing 1-methyl-1H-tetrazole through thermolysis elimination. Then, site-selectively carbophilic addition of sulfines by o-aryl diamines, followed by elimination, intramolecular nucleophilic addition and dehydration condensation. The current method provides a direct and simple strategy for the preparation of quinoxaline-2-thiols and quinoxalines.

A facile synthesis of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones and naphthoxazin-2-ones and their reactions with organolithium and Grignard reagents – Preparation of N-[1-(2′-hydroxyphenyl)alkyl]amides

2004 ◽  
Vol 82 (8) ◽  
pp. 1314-1321 ◽  
Author(s):  
Cristina Cimarelli ◽  
Gianni Palmieri ◽  
Emanuela Volpini
Keyword(s):  
Reaction Mechanism ◽  
Conformational Analysis ◽  
Grignard Reagents ◽  
Facile Synthesis ◽  
Simple Method ◽  
Relative Configuration ◽  
Organometallic Reagents ◽  
H Nmr ◽  
High Yields

A facile and simple method for the preparation of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones or naphthoxazin-2-ones in high yields from aminoalkylphenols and aminoalkylnaphthols is described. The reactions of the products obtained with organolithium and Grignard reagents were studied, and a method for the preparation of N-[1-(2-hydroxyphenyl)alkyl]-N-alkylamides, which are of pharmaceutical interest, from benzoxazinones was developed. A possible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of 1H NMR spectra.Key words: benzoxazinones, naphthoxazinones, organometallic reagents, amide preparation, aminoalkylphenols.

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