- Iron-Catalyzed Enantioselective Radical Carboazidation and Diazidation of α,β-Unsaturated Carbonyl Compounds
-
Azidation of alkenes is an efficient protocol to synthesize organic azides which are important structural motifs in organic synthesis. Enantioselective radical azidation, as a useful strategy to install a C-N3 bond, remains challenging due to the inherently instability and unique structure of radicals. Here, we disclose an efficient enantioselective radical carboazidation and diazidation of α,β-unsaturated ketones and amides catalyzed by chiral N,N′-dioxide/Fe(OTf)2 complexes. An array of substituted alkenes was transformed to the corresponding α-azido carbonyl derivatives in good to excellent enantioselectivities, benefiting the preparation of chiral α-amino ketones, vicinal amino alcohols, and vicinal diamines. Control experiments and mechanistic studies proved the radical pathway in the reaction process. The DFT calculations showed that the azido transferred to the radical intermediate via an intramolecular five-membered transition state with the internal nitrogen of the Fe-N3 species.
- Dong, Shunxi,Feng, Xiaoming,He, Jun,Liu, Wen,Liu, Xiaohua,Pu, Maoping,Wu, Yun-Dong,Zhang, Tinghui
-
supporting information
p. 11856 - 11863
(2021/08/16)
-
- Organocatalytic Stereoconvergent Synthesis of α-CF3 Amides: Triketopiperazines and Their Heterocyclic Metamorphosis
-
The highly enantioselective alkylation of α-CF3 enolates, generated from triketopiperazines, has been accomplished through use of a bifunctional thiourea organocatalyst to facilitate 1,4-addition to varied enone acceptors. On treatment with appropriate nitrogen nucleophiles, the chiral triketopiperazine products undergo a metamorphosis, to provide novel fused heterocyclic lactams such as extended pyrazolopyrimidines.
- Foster, Robert W.,Lenz, Eva N.,Simpkins, Nigel S.,Stead, Darren
-
supporting information
p. 8810 - 8813
(2017/07/11)
-
- Enantioselective Mannich Reaction Employing 1,3,5-Triaryl-1,3,5-triazinanes Catalyzed by Chiral-at-Metal Rhodium Complexes
-
Chiral-at-metal RhIII complexes catalyze the efficient enantioselective Mannich reaction of 2-acyl imidazoles with 1,3,5-triazinanes, affording the corresponding adducts in 81–99 % yield with up to >99 % enantioselectivity. This protocol performs with 0.1 mol-% of RhIII complex on gram scale without any loss in enantioselectivity.
- Gong, Jun,Li, Shi-Wu,Qurban, Saira,Kang, Qiang
-
supporting information
p. 3584 - 3593
(2017/07/22)
-
- 4,5- DIHYDROPYRAZOLE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THERAPY
-
The present invention relates to 4,5-dihydropyrazole derivatives of the formula (I) and physiologically tolerated salts thereof which are GlyT1 inhibitors. The invention further relates to pharmaceutical compositions comprising such 4,5-dihydropyrazole de
- -
-
Paragraph 0286; 0287; 0288; 0289
(2016/04/09)
-
- Iron-Catalyzed Michael Addition of Ketones to Polar Olefins
-
The base metal complex tetrabutylammonium nitrosyltricarbonylferrate {Bu4N[Fe(CO)3(NO)] (TBA[Fe])} – catalyzes the conjugate addition of ketones to polar olefins. The reaction is applicable to a wide range of substrates leading to interesting building blocks for organic synthesis. Clear indications for an acid-base type rather than a C?H activation pathway exist. (Figure presented.).
- Zhang, Di-Han,Knelles, Jakob,Plietker, Bernd
-
supporting information
p. 2469 - 2479
(2016/08/16)
-
- Use of NK-1 receptor antagonists in pruritus
-
The invention relates to methods for treating pruritus with an NK-1 receptor antagonist. The invention further relates to pharmaceutical compositions comprising NK-1 receptor antagonist.
- -
-
Page/Page column 6; 7
(2014/12/12)
-
- PYRIMIDINEDIONE COMPOUNDS AGAINST CARDIAC CONDITIONS
-
Provided are novel pyrimidine dione compounds and pharmaceutically acceptable salts thereof, that are useful for the treatment of hypertrophic cardiomyopathy (HCM) and conditions associated with left ventricular hypertrophy or diastolic dysfunction. The synthesis and characterization of the compounds and pharmaceutically acceptable salts thereof, are described, as well as methods for treating HCM and other forms of heart disease.
- -
-
Paragraph 0134-0135
(2015/01/07)
-
- Discovery of novel and potent heterocyclic carboxylic acid derivatives as protein tyrosine phosphatase 1B inhibitors
-
A series of novel heterocyclic carboxylic acid based protein tyrosine phosphatase 1B (PTP1B) inhibitors with hydrophobic tail have been synthesized and characterized. Structure-activity relationship (SAR) optimization resulted in identification of several
- Basu, Sujay,Prasad, Uppuleti Viplava,Barawkar, Dinesh A.,De, Siddhartha,Palle, Venkata P.,Menon, Suraj,Patel, Meena,Thorat, Sachin,Singh, Umesh P.,Sarma, Koushik Das,Waman, Yogesh,Niranjan, Sanjay,Pathade, Vishal,Gaur, Ashwani,Reddy, Satyanarayana,Ansari, Shariq
-
scheme or table
p. 2843 - 2849
(2012/05/20)
-
- Fe(II)-catalyzed amination of aromatic C-H bonds via ring opening of 2 H-azirines: Synthesis of 2,3-disubstituted indoles
-
A general method for the synthesis of 2,3-disubstituted indoles is described. The key feature of this method is the amination of aromatic C-H bonds via FeCl2-catalyzed ring opening of 2H-azirines. The method tolerates a variety of functional groups such as Br, F, NO2, OMe, CF3, OTBS, alkenes, and OPiv. The method can also be extended to synthesize azaindoles.
- Jana, Samaresh,Clements, MacK D.,Sharp, Barry K.,Zheng, Nan
-
supporting information; scheme or table
p. 3736 - 3739
(2010/11/03)
-
- Potent, brain-penetrant, hydroisoindoline-based human neurokinin-1 receptor antagonists
-
3-[(3aR,4R,5S,7aS)-5-{(1R)-1-[3,5-Bis(trifluoromethyl)phenyl]ethoxy} -4-(4-fluorophenyl)octahydro-2H-isoindol-2-yl]-cyclopent-2-en-1-one (17) is a high affinity, brain-penetrant, hydroisoindoline-based neurokinin-1 (NK1) receptor antagonist with a long ce
- Jiang, Jinlong,Bunda, Jaime L.,Doss, Geoge A.,Chicchi, Gary G.,Kurtz, Marc M.,Tsao, Kwei-Lan C.,Tong, Xinchun,Zheng, Song,Upthagrove, Alana,Samuel, Koppara,Tschirret-Guth, Richard,Kumar, Sanjeev,Wheeldon, Alan,Carlson, Emma J.,Hargreaves, Richard,Burns, Donald,Hamill, Terence,Ryan, Christine,Krause, Stephen M.,Eng, WaiSi,DeVita, Robert J.,Mills, Sander G.
-
experimental part
p. 3039 - 3046
(2010/03/03)
-
- POLYMORPHS OF A HYDROISOINDOLINE TACHYKININ RECEPTOR ANTAGONIST
-
This application is directed to a novel polymorph of a hydroisoindoline tachykinin receptor antagonist having the following structural formula A.
- -
-
Page/Page column 13-14
(2008/12/05)
-
- Process for making hydroisoindoline tachykinin receptor antagonists
-
The present invention is directed to a process for preparing certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The compounds are useful in the treatment of certain disorders, including emesis, urinary incontinence, depression, and anxiety.
- -
-
Page/Page column 7; 8
(2008/06/13)
-
- HYDROISOINDOLINE TACHYKININ RECEPTOR ANTAGONISTS
-
The present invention is directed to certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulati
- -
-
Page/Page column 16
(2008/06/13)
-
- Hydroisoindoline tachykinin receptor antagonists
-
The present invention is directed to certain hydroisoindoline compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulati
- -
-
Page/Page column 8
(2008/06/13)
-
- NITROGEN-CONTAINING HETEROARYL COMPOUNDS HAVING HIV INTEGRASE INHIBITORY ACTIVITY
-
A compound of the formula (I): wherein Z4, Z5 and Z9 each is independently carbon atom or nitrogen atom; Y is hydroxy, mercapto or amino; RA is a group of the formula: (wherein C ring is nitrogen-containing heteroaryl) has an inhibitory activity against integrase.
- -
-
-