Highly regioselective 1,3-dipolar cycloaddition of diphenylnitrilimine to Sc₃N@I_h-C₈₀ affording a very stable, unprecedented pyrazole-ring fused derivative of endohedral metallofullerenes

Abstract

Formation of a very stable, unprecedented pyrazole-ring fused derivative of endohedral metallofullerenes was achieved by the first 1,3-dipolar cycloaddition reaction of Sc3N@C80 with diphenylnitrilimine in a highly regioselective manner.

Photoreactions of Sc3N@Ih‐C80 and Lu3N@Ih‐C80 with disilirane: Isolation and characterization of labile 1,2‐adducts

“…The results indicate that 2b I and 2b IV, in which the Y‐shaped Sc 3 N clusters are oriented to straddle the addition sites, are the lowest and the second lowest in energy, respectively, among 2b I– 2b VI. This orientation of the Sc 3 N cluster is common to the [5,6]‐adducts of Sc 3 N@ I h ‐C 80 that were structurally determined by X‐ray crystallography [8a][8c] [9] [10b] [13] [14]…”

Synthesis of Spiro[Pyrrolo[2,1-b][1,3]Benzothiazole-3,2′-[1,3]Thiazolo[3,2-a] Pyrimidine] via Cycloaddition Reactions

“…[8][9][10] Thiazolo[3,2-a]pyrimidine derivatives are found in many synthetic derivatives due to their broad spectrum of biological activities, including as antagonists of 5HT2 serotonin receptors and dopamine D2 receptors, 11-12 antifungal 13 and antiinflammatory properties 14 and CDC25 phosphatase inhibitor activity. 15 In continuation of our work on the study of the cycloaddition reaction [16][17][18][19] , we now report the synthesis of spiro [thiazolo[3,2-a] pyrimidine] derivatives by the 1,3-dipolar cycloaddition reactions of azomethine ylide generated in situ by the reaction of 3-(4-methoxyphenacyl)benzothiazolium bromides and triethylamine with ethyl-5-aryl-2-[(Z)-2-methoxy-2oxoethylidene]-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a] pyrimidine-6-carboxylates (Scheme 1).…”

In Situ Generation of Nitrilimines from Aryldiazonium Salts and Diazo Esters: Synthesis of Fully Substituted Pyrazoles under Room Temperature

“…Notably, nitrilimines as a 1,3-dipole have shown unique potential, which could build diverse fully substituted pyrazoles . The most frequent method for the formation of nitrilimines was the dehydrohalogenation of hydrazonoyl halides (Scheme a) . However, the difficulties of preparing starting materials and the necessity of bases cannot be underestimated.…”