Diastereoselective synthesis of spiropyrazolones via 1,3-dipolar [3+2] cycloadditions between pyrazolone-based olefins and N, N’-cyclic azomethine imines

Synlett ◽  
2021 ◽  
Author(s):  
Hong-Wu Zhao ◽  
Zhe Tang ◽  
Hui-Hui Wu ◽  
Xiao-Zu Fan ◽  
Heng Zhang ◽  
...  

Under the catalysis of PhCO2H, the 1,3-dipolar [3+2] cycloaddition between pyrazolone-based olefins and N, N’-cyclic azomethine imines proceeded readily, thus delivering structurally novel spiropyrazolones with up to 98% yield and >20:1 dr. The relative stereochemical configuration of the obtained spiropyrazolones was unambiguously assigned by X-ray single crystal structure analysis. The diastereoselective formation of the title spiropyrazolones was interpreted by the hypothesized reaction mechanism.

Synlett ◽  
2021 ◽  
Author(s):  
Hong-Wu Zhao ◽  
Heng Zhang ◽  
Lu-Yu Cai ◽  
Zhe Tang ◽  
Xiao-Zu Fan ◽  
...  

Promoted by K2CO3 (2.0 equiv), the 1,3-dipolar [3+3] cycloaddition between 1, 4-benzodiazepinone-based nitrones and α-halohydroxamates processed smoothly under the mild reaction conditions and delivered structurally novel and complex cis or trans-configured d-edge-heterocycle-fused 1,4-benzodiazepinones in up to >99% isolated yield with >20:1 dr. The relative configuration of the title chemical entities was clearly identified with the use of X-ray single crystal structure analysis. The reaction mechanism was assumed to interpret the diastereoselective production of the obtained cis or trans-configured d-edge-heterocycle-fused 1, 4-benzodiazepinones.


2005 ◽  
Vol 60 (5) ◽  
pp. 569-571 ◽  
Author(s):  
Ali Ramazani ◽  
Ali Morsali ◽  
Bijan Ganjeie ◽  
Ali Reza Kazemizadeh ◽  
Ebrahim Ahmadi ◽  
...  

Selenourea reacts with dialkyl acetylenedicarboxylates under solvent-free conditions to form 1:1 adducts, which undergo a cyclization reaction to produce alkyl Z-2-(2-amino-4-oxo-1,3-selenazol- 5(4H)-ylidene)acetates, in good yields. The stereochemistry of the ethyl Z-2-(2-amino-4-oxo-1,3- selenazol-5(4H)-ylidene)acetate was established by X-ray single crystal structure analysis. The reaction is completely stereoselective.


Author(s):  
H. J. Berthold ◽  
E. Vonholdt ◽  
R. Wartchow ◽  
T. Vogt

AbstractNHA single crystal structure analysis of NThe deuterated compound NThe structures of the ordered low temperature phases will be reported separately.


Synlett ◽  
2021 ◽  
Author(s):  
Hong-Wu Zhao ◽  
Xiao-Fan Bi ◽  
Hai-Liang Pang ◽  
Zhe Tang ◽  
Heng Zhang ◽  
...  

In the presence of Na2CO3, the conjugate addition between α-halogeno hydrazones and nitroso compounds proceeded readily, thus delivering multifunctionalized nitrones in the reasonable chemical yields with excellent strereoselectivities. The chemical structure and stereochemical configuration of title chemical entities were unambiguously identified by an X-ray single crystal structure analysis.


1987 ◽  
Vol 109 (2) ◽  
pp. 592-594 ◽  
Author(s):  
Gert Admiraal ◽  
Johannis L. Van der Veer ◽  
Rudolf A. G. De Graaff ◽  
Jeroen H. J. Den Hartog ◽  
Jan Reedijk

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