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N-Heterocyclic Carbenes of 5-Haloindazoles Generated by Decarboxylation of 5-Haloindazolium-3-carboxylates
Syntheses and properties of 5-fluoro-, chloro- bromo-, and iodo-substituted 1,2-dimethyl indazolium-3-carboxylates as new representatives of pseudo-cross-conjugated heterocyclic mesomeric betainesExpand
Recent Advances in the Chemistry of Indazoles
Indazoles are of considerable interest due to the broad variety of their biological activities. This overview summarizes structures of pharmacologically interesting indazoles published during theExpand
Addition reactions and redox esterifications of carbonyl compounds by N-heterocyclic carbenes of indazole.
Thermal decarboxylation converts 1,2-dimethylindazolium-3-carboxylate into indazol-3-ylidene, which reacts in situ with ketones to form stable 1:1 adducts. When the reaction is conducted withExpand
Imidazol-2-and-4-ylidene by decarboxylation. Studies on the cross-conjugated mesomeric betaine-alkaloid norzooanemonine and its pseudo-cross-conjugated isomer.
1,3-Dimethylimidazolium-2-carboxylate and -4-carboxylate (norzooanemonine), which belong to two distinct classes of heterocyclic mesomeric betaines, undergo thermal decarboxylations to theExpand
Translation of pseudo-cross-conjugation into chemistry: cycloadditions of mesomeric betaines to the new ring system spiro[indazole-3,3'-pyrrole].
Indazolium-3-amidates (X-ray analysis), readily available on trapping the N-heterocyclic carbene indazol-3-ylidene with isocyanates, underwent [3+2]-cycloadditions with activated triple bonds toExpand
N-Heterocyclic Carbenesof Indazole: Ring Enlargement Reactions by α-HaloKetones and Dehalogenations of Vicinal Dihalides
On decarboxylation, l,2-dimethylindazolium-3-carboxylate forms the N-heterocyclic carbene, l,2-dimethylindazol-3-ylidene, which deprotonates α-halo ketones. The resulting indazolium salt and theExpand
Pseudo-Cross-Conjugated Mesomeric Betaines and N-Heterocyclic Carbenes of Indazole
1.2-Dimethylindazolium-3-carboxylates are pseudo-cross-conjugated mesomeric betaines (PCCMB) and derivatives of the indazole alkaloid Nigellicin. They decarboxylate on heating to give intermediaryExpand
N‐Heterocyclic Carbene Induced Cycloaddition Reactions of Indazoles with Acetylenes To Form a New Ring System
Thermal decarboxylation of the mesomeric betaine 1,2-dimethylindazolium-3-carboxylate resulted in the formation of the N-heterocyclic carbene indazol-3-ylidene which deprotonated a second molecule ofExpand
Quantum mechanical study and vibrational spectra of indazolium-3-carboxylate and its decarboxylation product, the N-heterocyclic carbene indazol-3-ylidene.
Indazolium-3-carboxylate is a molecule that can be found as the nucleus of several pseudo-cross-conjugated mesomeric betaines, such as the alkaloid nigellicine. From a chemical point of view, one ofExpand