94844-02-7Relevant academic research and scientific papers
Synthesis, Reactivity, Functionalization, and ADMET Properties of Silicon-Containing Nitrogen Heterocycles
Barraza, Scott J.,Denmark, Scott E.
supporting information, p. 6668 - 6684 (2018/06/12)
Silicon-containing compounds have been largely ignored in drug design and development, despite their potential to improve not only the potency but also the physicochemical and ADMET (absorption, distribution, metabolism, excretion, toxicity) properties of drug-like candidates because of the unique characteristics of silicon. This deficiency is in large part attributable to a lack of general methods for synthesizing diverse organosilicon structures. Accordingly, a new building block strategy has been developed that diverges from traditional approaches to incorporation of silicon into drug candidates. Flexible, multi-gram-scale syntheses of silicon-containing tetrahydroquinoline and tetrahydroisoquinoline building blocks are described, along with methods by which diversely functionalized silicon-containing nitrogen heterocycles can be rapidly built using common reactions optimized to accommodate the properties of silicon. Furthermore, to better clarify the liabilities and advantages of silicon incorporation, select compounds and their carbon analogues were challenged in ADMET-focused biological studies.
Insight into O2-promoted base-catalyzed N-alkylation of amines with alcohols
Wang, Chao,Chen, Changpeng,Han, Jian,Zhang, Jingyu,Yao, Yingming,Zhao, Yingsheng
supporting information, p. 2972 - 2977 (2015/04/27)
A highly efficient and practical transition-metal-free CsOH/O2 catalyst system was developed for the N-alkylation of amines with alcohols under argon. This strategy was compatible with many alcohols and exhibits excellent functional group tolerance. More significantly, the selective formation of secondary amines was achieved in excellent yields. The detailed mechanistic study gave a clear understanding of the role of base and oxygen in the catalytic cycle.
X-ray and 1H NMR Studies of the Conformational Equilibria of 2-Z-3-Phenyl-1,3,2-oxazaphosphorinanes. Steric and Stereoelectronic Influences on the Unexpected Axial Preferences of Me2N and MeNH Substituents on Three-Coordinate Phosphorus
Huang, Yande,Arif, Atta M.,Bentrude, Weseley G.
, p. 6235 - 6246 (2007/10/02)
A series of 2-Z-3-phenyl-1,3,2-oxazaphosphorinanes 7-14 (Z = MeO, (CF3)2CHO, Ph, MeNH, and Me2N) containing three-coordinate phosphorus was prepared.The conformations of the six-membered rings were investigated by 1H and 31P NMR spectroscopy and X-ray cry
Ketene. Part 26. The Reactions of 3,4-Dihydroisoquinoline N-Oxide with Ketenes, and an Attempted Synthesis of 3,4-Dihydro-3,3-dimethylquinoline N-Oxide
Evans, Andrew R.,Martin, Russell,Taylor, Giles A.,Yap, C. H. Maurice
, p. 1635 - 1640 (2007/10/02)
3,4-Dihydroisoquinoline N-Oxide reacts with dimethylketene to form a 1:2 adduct (8) in addition to compounds (6) and (7).With cyano-t-butylketene and ethoxycarbonyl-t-butylketene the adducts (9a) and (9b) are formed. 3,3-Dimethyl-1,2,3,4-tetrahydroquinoline (21a) has been synthesized, but attempts to convert this into the nitrone (20b) were unsuccessful.
CONFORMATIONS OF SATURATED SIX-MEMBERED-RING PHOSPHOROUS HETEROCYCLES. CHAIR-CHAIR EQUILIBRIA FOR CYCLOPHOSPHAMIDE, THE 5,5-DIMETHYL DERIVATIVE, AND RELATED 1,3,2-OXAZAPHOSPHORINANES. RELATIVE CONFORMATIONAL ENERGIES OF NITROGEN MUSTARD AND OTHER R2<
Setzer, William N.,Sopchik, Alan E.,Bentrude, Wesley G.
, p. 2083 - 2091 (2007/10/02)
A series of 5,5-dimethyl-3-R-2-oxo-2-Z-1,3,2-oxazaphosphorinanes (1, R= H, Z= Me2N; 2, R= H, Z= Et2N; 3, R= H, Z= i-Pr2N; 4, R= H, Z= N(CH2CH2Cl)2; 5, R= Ph,Z= Me2N) has been prepared, and their conformations have been studied by 1H NMR at 300 MHz.The pos
