1079-46-5Relevant articles and documents
Quantum mechanical study and vibrational spectra of indazolium-3- carboxylate and its decarboxylation product, the N-heterocyclic carbene indazol-3-ylidene
Schmidt, Andreas,Snovydovych, Bohdan,Casado, Juan,Quirante, Jose Joaquin,Navarrete, Juan Teodomiro Lopez,Ramirez, Francisco Javier
, p. 341 - 348 (2009)
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 of the more interesting properties of this class of molecules is the possibility of forming an N-heterocyclic carbene by thermal decarboxylation. In this paper we have studied the carbene generation by decarboxylation of 1,2-dimethyl indazolium-3- carboxylate, using vibrational (infrared and Raman) spectroscopy and quantum chemistry calculations. Normal mode analysis allowed us to analyse the changes in the stretching force constants upon decarboxylation and to establish spectroscopic-structure relationships. We also investigate the effect of 5-halogen (fluoro, chloro) substitution on the carbene generation. Decarboxylation energy profiles of the three derivatives were calculated. Crossing of the energy paths when going from the transition state to the final product were obtained. The theoretical tendency found for the activation energies agrees with that observed for the decarboxylation temperatures and for the calculated NICS values of the benzene moieties. the Owner Societies.
THERAPEUTIC INHIBITORY COMPOUNDS
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Page/Page column 97, (2015/07/16)
The invention provides compounds of Formula I and Formula II: A-B-C-D-E-F-G-J (I) C-D-E-F-G-J (II) wherein A, B, C, D, E, F, G, and J have any of the values defined in the specification, and salts thereof. The compounds are useful for inhibiting plasma kallikrein, and for treating a disease or condition in an animal where inhibition of plasma kallikrein is indicated.
N-heterocyclic carbenes of 5-haloindazoles generated by decarboxylation of 5-haloindazolium-3-carboxylates
Schmidt, Andreas,Snovydovych, Bohdan,Habeck, Tobias,Droettboom, Petra,Gjikaj, Mimoza,Adam, Arnold
, p. 4909 - 4916 (2008/03/14)
Syntheses and properties of 5-fluoro-, chloro- bromo-, and iodo-substituted 11,2-dimethylindazohum-3-carboxylates as new representatives of pseudo-cross-conjugated heterocyclic mesomeric betaines are described, and results of an X-ray single crystal analy