Structure and Reactivity of Bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) Acid Hydrazide

Abstract

Establishing of the structure of hydrazinolysis product obtained from bicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) acid was performed by preparation of the compound under alternative conditions followed by comparison of the characteristics and spectral parameters of the resulting substances, and also by quantum-chemical calculations by the density functional method of the chemical shifts in 1 H and 13 C NMR spectra of different reaction products. The X-ray diffraction analysis of the hydrazide was also carried out. The compound obtained was assigned a structure of N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide. The products were prepared by its reactions with arylsulfonyl chlorides, benzoyl chlorides, m-tolyl and p-toluenesulfonyl isocyanates, phenyl isothiocyanate, with o-nitrobenzaldehyde, and oxiranes (1,2-epoxycyclohexane and 2,3-epoxypropylcarbazole). The aromatic sulfonamides, carboxamides, and ureas were epoxidized by performic acid obtained in situ from the formic acid and hydrogen peroxide. Products of [3+2]-cycloaddition of aryl azides to the strained double bond in the N-aminobicyclo[2.2.1] hept-2-ene-endo-5,endo-6-dicarboximide and its derivatives. The structures of compounds obtained were confirmed by their IR, 1 H and 13 C NMR spectra.

Synthesis of new N-norbornylimide substituted amide derivatives, their reductive Heck and domino Heck reactions

“…27 Thereafter, compound 2 was obtained from the reaction of hydrazonium chloride and compound 1 in toluene at room temperature. 28 We continued to prepare the optically active norbornenylimide substituted acid 3 from 1 using Amos' procedure. 29 As the last step of this part, we synthesized a new norbornenylimide acyl chloride derivative 4 from 3 in an excellent yield.…”

Cage-like amino alcohols. synthesis, reactions, and application

“…Epoxide 62 reacted with bicyclic amines to give amino alcohols 63-65 [39] whose structure was confirmed by IR and NMR spectra. Reactions of N-aminobicyclo[2.2.1]hept-2-ene-endo-5,endo-6-dicarboxylic (endic) acid imide (66) were reported [66]. Studies have been initiated on reactions of cage-like amines with novel epoxy compounds having O-and N- (2,3-epoxypropyl) fragments [67].…”

Synthesis and Anticancer Evaluation of Benzimidazole Derivatives Having Norbornene/Dibenzobarrelene Skeletons and Different Functional Groups

“…All the spectroscopic data for these compounds are in agreement with the expected structures. Most of the synthesized compounds are new derivatives of benzimidazole, except compounds 1, [18] 2, [19] and 14 [20] which were described in the literature [21] . The anti‐growth effects of synthesized benzimidazole derivatives (compounds 4–20) were investigated against MDA‐MB‐231, A549, Panc1, and Ovcar3 cell lines with 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) analysis [22–25] …”