33107-14-1Relevant academic research and scientific papers
Structural verification of a tetrahydrotetrazole compound
Breton, Gary W.,Hahn, Lauren A.,Martin, Kenneth L.
, p. 1208 - 1212 (2019/09/18)
Tetrahydrotetrazoles are five-membered-ring heterocycles containing four contiguous saturated nitrogen atoms. Very few examples of such compounds have been reported in the literature. Our previous attempt at the synthesis of a member of this class of compound suggested that the N - N bonds may be more labile than expected. This finding raised the question as to whether the structures of any of the previously reported tetrahydrotetrazoles had been properly assigned. We have reproduced the synthesis of a reported tetrahydrotetrazole, namely 1,2-di-tert-butyl 3-phenyl-1H,2H,3H,10bH-[1,2,3,4]tetrazolo[5,1-a]isoquinoline-1,2-dicarboxylate, C25H30N4O4, and have now confidently confirmed its structure via X-ray crystallography. However, while sufficiently stable in the crystal phase, we discovered that it remains very labile in solution (having a half-life of only 15min at 20°C in CDCl3). A tentative reaction pathway for its dissociation based on 1H NMR spectral evidence is provided.
Synthesis of Tetrahydroisoquinoline Alkaloids and Related Compounds through the Alkylation of Anodically Prepared α-Amino Nitriles
Benmekhbi, Lotfi,Louafi, Fadila,Roisnel, Thierry,Hurvois, Jean-Pierre
, p. 6721 - 6739 (2016/08/16)
α-Amino nitrile 2a was conveniently prepared in two individual steps from chiral hexafluorophosphate salt isoquinolinium (-)-8b including anodic cyanation as an efficient means to activate the sp3 C1-H bond of the THIQ nucleus. The lithiation o
Isoquinolin-1-ylidenes as electronically tuneable ligands
Gomez-Bujedo, Silvia,Alcarazo, Manuel,Pichon, Christophe,Alvarez, Eleuterio,Fernandez, Rosario,Lassaletta, Jose M.
, p. 1180 - 1182 (2008/02/02)
The novel isoquinolin-1-ylidene ligands, introduced into Rh(i) complexes by exploiting the carbene-like reactivity of adducts 6, exhibit ligand properties similar to those of classic NHCs, and their electronic properties can be tuned by the introduction o
The Solid-Phase Zincke Reaction: Preparation of ω-Hydroxy Pyridinium Salts in the Search for CFTR Activation
Eda, Masahiro,Kurth, Mark J.,Nantz, Michael H.
, p. 5131 - 5135 (2007/10/03)
A study of structural modifications of MPB-07 was undertaken as part of a synthetic program aimed at discovering small molecules with CFTR activation potential. Solid-phase synthesis techniques were used to prepare derivatives of MPB-07 employing the Zincke reaction for the construction of aromatic, quaternary ammonium salts such as those found in 2 or 3. In this transformation, primary amines react with highly electrophilic N-2,4-dinitrophenylpyridinium (DNP) salt 4 to afford pyridinium salt 8 with release of 2,4-dinitroaniline 6. Thus, the reaction of 1-(2,4-dinitrophenyl)pyridinium salts with various polymer-bound amino ethers, followed by cleavage from the resin, delivers the desired salts in good yield and high purity.
Application of High-Resolution Solid State NMR Spectroscopy for the Determination of the Ring - Chain Tautomerism
Kessler, Horst,Oschkinat, Hartmut,Zimmermann, Gottfried,Moehrle, Hans,Biegholdt, Martin,et al.
, p. 702 - 709 (2007/10/02)
The structure of the benzaldehyde derivatives 1 and 2 showing ring-chain tautomerism was investigated by NMR spectroscopy in the solid state and in solution.Difficulties in preparing single crystals, low solubility, and the presence of solvent in the crys
