14468-90-7Relevant articles and documents
Studies toward gymnodimine: development of a single-pot Hua reaction for the synthesis of highly hindered cyclic imines.
Ahn,Cardenas,Yang,Romo
, p. 751 - 754 (2001)
[structure: see text]. In studies directed toward gymnodimine and related marine toxins, a single-pot variation of the Hua cyclic imine synthesis has been developed. The reaction involves generation of N-trimethylsilyl lactams in situ followed by alkyllithium addition leading directly to cyclic imines. Importantly, this reaction proceeds efficiently with highly hindered alpha,alpha-dialkyl lactams, provided 1,2-dimethoxyethane (DME) is used as solvent, leading to stable cyclic imines. Overall, this transformation allows a one-pot coupling of an alkyliodide and a lactam to give a cyclic imine.
Lactamomethylsilanes – Synthesis, Structures, and Reactivity towards CO2 and Phenylisocyanate
Herbig, Marcus,B?hme, Uwe,Kroke, Edwin
, p. 377 - 387 (2019)
Lactamomethylsilanes of γ-butyrolactam, δ-valerolactam, ε-caprolactam, and 1-isoindolinone (phthalimidine) with up to three methyl moieties were synthesized according to the chemical formula MexSiLac(4–x) (x = 0, 1, 2, and 3). Using the lactams as starting materials four synthetic routes were tested: salt elimination, transsilylation, transamination, and metallation of the lactames followed by reaction with methylchlorosilanes. All products were analyzed by NMR (1H, 13C and 29Si) and RAMAN spectroscopy. Selected solid products were crystallized and the molecular structure was determined by single-crystal X-ray diffraction. The reactivity of the lactamomethylsilanes towards phenylisocyanate and CO2 was studied.
A double alkylation - Ring closing metathesis approach to spiroimines
Brimble, Margaret A.,Trzoss, Michael
, p. 5613 - 5622 (2004)
As part of a programme directed towards the synthesis of the marine toxins, the spirolides and gymnodimine, a convenient synthesis of the key bicyclic spiroimine ring systems has been developed. The method involves double alkylation of a simple lactam, Grubbs ring closing metathesis of the resultant dialkylated lactam then reduction of the lactam to an imine.
Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives
Szalay, Roland,Harmat, Veronika,E?ri, János,Pongor, Gábor
supporting information, p. 2186 - 2192 (2017/05/16)
A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.
COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
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Page/Page column 140, (2011/07/07)
Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
