PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α-Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3H)-ones

Author(s):  
Baibin Li ◽  
Jingwen Yuan ◽  
Xuebei Ye ◽  
Rui Zhang ◽  
Jiacheng Li ◽  
...  
Keyword(s):  
2019 ◽  
Vol 16 (6) ◽  
pp. 511-516
Author(s):  
Adnan Cetin

Efficient steps towards the synthesis of novel (phenyl)(1'-aryl-1,5,5'-triphenyl[3,3'-bi-1Hpyrazol]- 4-yl)methanones 4a-e were developed. The procedure starts from 1-(4-benzoyl-1,5-diphenyl- 1H-3-pyrazolyl)-3-phenyl-2-propyn-1-one (2) which was synthesized by a palladium catalyzed crosscoupling reaction. Compound 2 reacted with various hydrazines to give (E)-(phenyl)[1,5-diphenyl-3- [3-phenyl-1-(2-arylhydrazono)-2-propyn-1-yl]-1H-4-pyrazolyl]methanones E-3a-e. The bis-pyrazole derivatives 4a-e were synthesized from electrophilic cyclization reaction of α,β-acetylenic hydrazones E-3a-e and copper(I) iodide. All synthesized compounds were characterized by FT-IR, 1H, 13C NMR and Mass spectral analyses.


2019 ◽  
Vol 84 (21) ◽  
pp. 13871-13880 ◽  
Author(s):  
Xie-Chao Yang ◽  
Jin-Yu Liu ◽  
Zhen Liu ◽  
Xiu-Qin Hu ◽  
Peng-Fei Xu

2020 ◽  
Vol 304 ◽  
pp. 127382 ◽  
Author(s):  
Li Fu ◽  
Chunfei Chen ◽  
Wenqiang Chen ◽  
Jun Huang ◽  
Junan Xiao ◽  
...  
Keyword(s):  

2003 ◽  
Vol 5 (17) ◽  
pp. 3017-3020 ◽  
Author(s):  
Kiyosei Takasu ◽  
Hiroshi Ohsato ◽  
Masataka Ihara
Keyword(s):  

2021 ◽  
Vol 363 (4) ◽  
pp. 1038-1043
Author(s):  
Ying‐Chun He ◽  
Yan‐Mei Yan ◽  
Zhen‐Xing Ren ◽  
Yong‐Zhao Wang ◽  
Qiang Yu ◽  
...  

2021 ◽  
Vol 23 (4) ◽  
pp. 1451-1456
Author(s):  
Hai-Jun Leng ◽  
Qing-Zhu Li ◽  
Peng Xiang ◽  
Ting Qi ◽  
Qing-Song Dai ◽  
...  

Author(s):  
Huiqing Chen ◽  
Jie Tang ◽  
Ting Liu ◽  
Li-Fang Yu ◽  
Dong Xing ◽  
...  

Herein we report an enantioselective method for the rapid construction of chiral 3-nitro-4-chromanones via a chiral thiourea-catalyzed intramolecular Michael-type cyclization reaction. With this method, a series of 3,3-disubstituted-3-nitro-4-chromanones bearing contiguous...


Synthesis ◽  
2020 ◽  
Author(s):  
Feng Li ◽  
Hai Ma ◽  
Qing-he Zhao ◽  
Guang-hao Yu ◽  
Ye-chen Meng ◽  
...  

AbstractA series of (trifluoromethyl)cyclopropanes (TFCPs) tolerating a broad range of functional groups, known as tert-butyl bioisosteres, have been obtained from the cyclization reaction between nitromethane­ and 5-[β-(trifluoromethyl)styryl]isoxazoles in 70–94% yields and 75:25 to 90:10 dr. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing an inorganic base under phase-transfer conditions.


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