20962-70-3Relevant academic research and scientific papers
Homologation of Electron-Rich Benzyl Bromide Derivatives via Diazo C-C Bond Insertion
Modak, Atanu,Alegre-Requena, Juan V.,De Lescure, Louis,Rynders, Kathryn J.,Paton, Robert S.,Race, Nicholas J.
supporting information, p. 86 - 92 (2021/12/27)
The ability to manipulate C-C bonds for selective chemical transformations is challenging and represents a growing area of research. Here, we report a formal insertion of diazo compounds into the "unactivated"C-C bond of benzyl bromide derivatives catalyzed by a simple Lewis acid. The homologation reaction proceeds via the intermediacy of a phenonium ion, and the products contain benzylic quaternary centers and an alkyl bromide amenable to further derivatization. Computational analysis provides critical insight into the reaction mechanism, in particular the key selectivity-determining step.
Iodine-Catalyzed Synthesis of Substituted Furans and Pyrans: Reaction Scope and Mechanistic Insights
Pace, Domenic P.,Robidas, Rapha?l,Tran, Uyen P. N.,Legault, Claude Y.,Nguyen, Thanh Vinh
, p. 8154 - 8171 (2021/06/28)
Substituted pyrans and furans are core structures found in a wide variety of natural products and biologically active compounds. Herein, we report a practical and mild catalytic method for the synthesis of substituted pyrans and furans using molecular iodine, a simple and inexpensive catalyst. The method described is performed under solvent-free conditions at an ambient temperature and atmosphere, thus offering a facile and practical alternative to currently available reaction protocols. A combination of experimental studies and density functional theory calculations revealed interesting mechanistic insights into this seemingly simple reaction.
BENZOQUINOLINE INHIBITORS OF VESICULAR MONOAMINE TRANSPORTER 2
-
Paragraph 0246; 0247, (2018/07/05)
The present invention relates to new benzoquinoline inhibitors of vesicular monoamine transporter 2 (VMAT2), pharmaceutical compositions thereof, and methods of use thereof.
A distinctive transformation based diversity oriented synthesis of small ring carbocycles and heterocycles from biocatalytically derived enantiopure α-substituted-β-hydroxyesters
Halder, Joydev,Das, Debabrata,Nanda, Samik
, p. 2549 - 2575 (2018/04/12)
A series of structurally novel small ring carbocyclic and heterocyclic molecules were accessed in an enantiopure fashion. The starting materials, α-substituted-β-hydroxyesters, were achieved through the biocatalytic dynamic kinetic resolution of parent β-
BENZOQUINOLONE INHIBITORS OF VMAT2
-
Paragraph 00107, (2015/04/15)
The present invention relates to new benzoquinolone inhibitors of VMAT2, pharmaceutical compositions thereof, and methods of use thereof represented by structural Formula I.
METHODS OF TREATING ABNORMAL MUSCULAR ACTIVITY
-
Paragraph 0206, (2015/06/08)
Methods for treating abnormal muscular activity are disclosed. The methods may be performed remotely and permit monitoring of a subject outside a healthcare provider's office.
BENZOQUINOLINE INHIBITORS OF VESICULAR MONOAMINE TRANSPORTER 2
-
Paragraph 00174, (2015/06/08)
The present invention relates to new benzoquinoline inhibitors of vesicular monoamine transporter 2 (VMAT2), pharmaceutical compositions thereof, and methods of use thereof. (I)
BENZOQUINOLINE INHIBITORS OF VESICULAR MONOAMINE TRANSPORTER 2
-
Paragraph 00200, (2015/08/06)
The present invention relates to new benzoquinoline inhibitors of vesicular monoamine transporter 2 (VMAT2), pharmaceutical compositions thereof, and methods of use thereof. (Formula (I))
Three-step synthetic pathway to fused bicyclic hydantoins involving a selenocyclization step
?mit, Biljana M.,Pavlovi?, Radoslav Z.
, p. 1101 - 1108 (2015/01/30)
Sequential 5-alkenyl hydantoin and pyrrolidine ring-forming reactions have been applied in the synthesis of conformationally constrained fused bicyclic scaffold. They are assembled by a three-step reaction sequence from two variable building blocks (readily available β-ketoesters and alkenyl halides) by combining a Bucherer-Bergs reaction with a final selenium-promoted intramolecular cyclization as a key step. The chemoselectivity of this bicyclic hydantoin formation is strongly influenced by experimental factors such as the solvent and the use of additives. The reaction is regiospecific giving only five-membered fused bicyclic hydantoins in good to excellent yields stemming from the nucleophilic attack of the nitrogen atom to a cyclic seleniranium ion intermediate during the cyclization step. A separable diastereomeric mixture is obtained; the products with bridgehead substituents and phenylseleno groups in cis relationships were formed predominantly. The reaction tolerates a variety of substitution at the double bond, furthermore, the presence of substituents at C(5) and N(3) position opens up the capability of generating a broad structural diversity.
Dual platinum and pyrrolidine catalysis in the direct alkylation of allylic alcohols: Selective synthesis of monoallylation products
Shibuya, Ryozo,Lin, Lu,Nakahara, Yasuhito,Mashima, Kazushi,Ohshima, Takashi
supporting information, p. 4377 - 4381 (2014/05/06)
A dual platinum- and pyrrolidine-catalyzed direct allylic alkylation of allylic alcohols with various active methylene compounds to produce products with high monoallylation selectivity was developed. The use of pyrrolidine and acetic acid was essential, not only for preventing undesirable side reactions, but also for obtaining high monoallylation selectivity. Two cats are better than one: The combined use of platinum and pyrrolidine catalysts enabled the direct alkylation of allylic alcohols with reactive methylene compounds. Pyrrolidine was essential for obtaining high selectivity of the monoallylation products, which were produced without the use of excess nucleophiles. cod=1,5- cyclooctadiene, EWG=electron-withdrawing group.
