Regioselective synthesis and DFT computational studies of novel β-hydroxy-1,4-disubstituted-1,2,3-triazole-based benzodiazepinediones using click cycloaddition reaction

2021 ◽  
Author(s):  
Hossein Paghandeh ◽  
Maryam Khalili Foumeshi ◽  
Hamid Saeidian
Keyword(s):  
Cycloaddition Reaction ◽  
Regioselective Synthesis ◽  
Computational Studies

scholarly journals SET activation of nitroarenes by 2-azaallyl anions as a straightforward access to 2,5-dihydro-1,2,4-oxadiazoles

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Dong Zou ◽  
Lishe Gan ◽  
Fan Yang ◽  
Huan Wang ◽  
Youge Pu ◽  
...  
Keyword(s):  
Transition Metal ◽  
Experimental Evidence ◽  
Radical Anion ◽  
Reaction Pathway ◽  
Cycloaddition Reaction ◽  
Electron Donors ◽  
Ring Closure ◽  
Computational Studies ◽  
Metal Free ◽  
Radical Coupling

AbstractThe use of nitroarenes as amino sources in synthesis is challenging. Herein is reported an unusual, straightforward, and transition metal-free method for the net [3 + 2]-cycloaddition reaction of 2-azaallyl anions with nitroarenes. The products of this reaction are diverse 2,5-dihydro-1,2,4-oxadiazoles (>40 examples, up to 95% yield). This method does not require an external reductant to reduce nitroarenes, nor does it employ nitrosoarenes, which are often used in N–O cycloadditions. Instead, it is proposed that the 2-azaallyl anions, which behave as super electron donors (SEDs), deliver an electron to the nitroarene to generate a nitroarene radical anion. A downstream 2-azaallyl radical coupling with a newly formed nitrosoarene is followed by ring closure to afford the observed products. This proposed reaction pathway is supported by computational studies and experimental evidence. Overall, this method uses readily available materials, is green, and exhibits a broad scope.

Facile Regioselective Synthesis of 1,2,6,8-Tetraazaspiro[4.4]nona-2,6-dien-9-ones

2000 ◽  
Vol 55 (2) ◽  
pp. 222-226 ◽  
Author(s):  
Adel S. Girgis
Keyword(s):  
Cycloaddition Reaction ◽  
Regioselective Synthesis ◽  
Dipolar Cycloaddition

1,3-Dipolar cycloaddition reaction of nitrilimines to a variety of 3-aryl-5-arylmethylidene- 3,5-dihydro-2-phenyl-4H-imidazol-4-ones (3) afforded the corresponding 1,3,4,7,8-pentaaryl -1,2,6,8-tetraazaspiro[4.4]-nona-2,6-dien-9-ones (4) and not the regio-isomers 2,3,6,8,9-pentaaryl- 1,3,7,8-tetraazaspiro[4.4]nona-1,6-dien-4-ones (5) in high regioselectivity.

Regioselective Synthesis of Novel Spirooxindolo and Spiroindano Nitro Pyrrolidines Through 3+2 Cycloaddition Reaction

2006 ◽  
Vol 36 (2) ◽  
pp. 141-150 ◽  
Author(s):  
Mahalingam Poornachandran ◽  
Rajendran Muruganantham ◽  
Ragavachary Raghunathan
Keyword(s):  
Cycloaddition Reaction ◽  
Regioselective Synthesis

ChemInform Abstract: A Multicomponent Pathway-Inspired Regioselective Synthesis of 2,3,4-Trisubstituted 1H-Pyrroles via [3 + 2] Cycloaddition Reaction.

ChemInform ◽  
2015 ◽  
Vol 46 (43) ◽  
pp. no-no
Author(s):  
Hanuman P. Kalmode ◽  
Kamlesh S. Vadagaonkar ◽  
Kaliyappan Murugan ◽  
Atul C. Chaskar
Keyword(s):  
Cycloaddition Reaction ◽  
Regioselective Synthesis

A Regioselective Synthesis of Carbazole‐Appended Dispiropyrrolothiazoles/Pyrrolidines: Synthesis, Computational Studies and In Vitro Anticancer Activity

2019 ◽  
Vol 4 (33) ◽  
pp. 9540-9549
Author(s):  
Kripalaya Ratheesh Arya ◽  
Hazel A. Sparkes ◽  
Baskaran Vijaya Pandiyan ◽  
Karnam Jayarampillai Rajendra Prasad
Keyword(s):  
Anticancer Activity ◽  
Regioselective Synthesis ◽  
Computational Studies
Sign in / Sign up

Export Citation Format

Share Document