- Proline-catalyzed sequential syn-Mannich and [4 + 1]-annulation cascade reactions to form densely functionalized pyrrolidines
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A highly efficient one-pot [4 + 1]-annulation process for the asymmetric synthesis of densely functionalized pyrrolidine derivatives is described. The in situ generated syn-Mannich adduct obtained via proline catalysis acts as a four-atom component, and Corey's sulfur ylide or ethyl bromoacetate acts as a one-atom carbon source to construct pyrrolidine units in a highly enantio- and diastereoselective manner.
- Aher, Ravindra D.,Kumar, B. Senthil,Sudalai, Arumugam
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- Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents
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The development of a copper-catalyzed cross-coupling between primary and secondary (pseudo)halides and bicyclopentyl Grignard reagents is reported. Highly strained bicyclopentanes can be cross-coupled with a large panel of primary alkyl mesylates and secondary alkyl iodides. The catalytic system is simple and cheap, and the reaction is general and chemoselective.
- Andersen, Claire,Bernardelli, Patrick,Cossy, Janine,Daumas, Marc,Ferey, Vincent,Guérinot, Amandine
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supporting information
(2020/08/05)
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- A visible-light photoinduced charge-transfer complex promoted the ring opening of: N-alkyl-4-piperidinols
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A visible-light photoinduced ring opening of N-alkyl-4-piperidinols under mild conditions has been achieved. The reaction sequence involves a visible-light-induced charge-transfer complex, which promoted the S-Cl bond cleavage of sulfonyl chlorides. The generated sulfonyl radical further reacts with N-alkyl-4-piperidinol cation radicals to achieve C-N and C-C bond cleavages to yield homoallylamine products.
- Du, Zhengyin,Fu, Ying,Huo, Congde,Shi, Chun-Zhao,Xu, Qin-Shan
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supporting information
p. 2264 - 2269
(2020/04/21)
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- New IDO-1 INHIBITOR AND USE THEREOF
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The present invention refers to inhibit iDO-a 1 number and their use relates to search, more particularly by inhibiting the activity of the intracellular enzyme IDO (indoleamine-a 2,3 a-dioxygenase), which show excellent iDO-a 1 billion number number inhi
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Paragraph 0551; 0570; 0571; 0572
(2017/06/27)
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- Boron trifluoride etherate functioning as a fluorine source in an iodosobenzene-mediated intramolecular aminofluorination of homoallylic amines
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A widely used Lewis acid BF3·Et2O was shown to be capable of acting as an efficient fluorinating agent in an intramolecular aminofluorination reaction of homoallylic amines to provide 3-fluoropyrrolidines mediated by a commercially available hypervalent iodine(III) reagent PhIO at room temperature. A mechanism involving a carbocation intermediate was proposed on the basis of several experimental evidence.
- Cui, Jian,Jia, Qun,Feng, Ruo-Zhu,Liu, Shan-Shan,He, Tian,Zhang, Chi
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supporting information
p. 1442 - 1445
(2014/04/03)
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- A smooth rearrangement of N-p-toluenesulfonyl 2-tert- butyldiphenylsilylmethyl-substituted azetidines into N-p-toluenesulfonyl 3-tert-butyldiphenylsilyl-substituted pyrrolidines
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The rearrangement of N-p-toluenesulfonyl 2-tert-butyldiphenylsilylmethyl- substituted azetidines into 3-tert-butyldiphenylsilyl-substituted pyrrolidines under Lewis acid conditions in dichloromethane involves 1,2-migration of silicon through a siliranium ion. The formation of siliranium ion was discovered not to be in concert with σC-N cleavage from stereochemical analysis of the pyrrolidine products formed from 3- and 4-substituted-2-tert- butyldiphenylsilylmethyl azetidines and also from the optical rotation data and chiral HPLC analysis of the pyrrolidine product formed from N-p-toluenesulfonyl 2(R)-tert-butyldiphenylsilylmethyl azetidine. The formation of sterically less hindered siliranium ion is followed by its SN2 opening by the internal nitrogen nucleophile. Oxidative cleavage of σC-Si bond leads to the formation of 3-hydroxypyrrolidines.
- Narhe, Bharat D.,Sriramurthy, Vardhineedi,Yadav, Veejendra K.
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experimental part
p. 4390 - 4399
(2012/07/14)
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- 3-Hydroxypyrrolidines from epoxysulfonamides and dimethylsulfoxonium methylide
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N-Tosyl-protected 3-hydroxypyrrolidines are prepared by reaction of dimethylsulfoxonium methylide with readily available epoxysulfonamides. The Royal Society of Chemistry 2006.
- Hodgson, David M.,Fleming, Matthew J.,Xu, Zhaoqing,Lin, Changxue,Stanway, Steven J.
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p. 3226 - 3228
(2008/09/18)
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- N-Substituted-3-arylpyrrolidines: Potent and Selective Ligands at Serotonin 1A Receptor
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3-Arylpyrrolidines are synthesized through the coupling of N-benzyl-3-(methanesulfonyloxy)pyrrolidine with diarylcuprates. Pharmacological evaluation of a series of N-substituted-3-arylpyrrolidines toward several neurotransmitter receptors indicated that some of them are good ligands for serotonin 1A receptor. Particularly, N-pyrrolidines were found to be potent and selective ligands. A preliminary biological evaluation for several selected compounds indicated that they are potentially effective antianxiety and antidepressant agents.
- Ahn, Kyo Han,Lee, Seok Jong,Lee, Chang-Ho,Hong, Chang Y.,Park, Tae Kyo
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p. 1379 - 1384
(2007/10/03)
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- SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 1-CYCLOPROPYL-6,8-DIFLUORO-7-(2-SUBSTITUTED 4,6-DIHYDRO-1H-PYRROLOTHIAZOL-5-YL)-1,4-DIHYDRO-4-OXOQUINOLINE-3-CARBOXYLIC ACID
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Quinolone derivatives (9 and 10) substituted with bicyclothiazole (7) and (8) at C-7 position were synthesized.Bicyclothiazole derivatives (7 and 8) were prepared through 9 steps by way of the 4-bromo-3-oxopyrrolidine (16) was a key intermediate and intro
- Kim, Wan-Joo,Kim, Bong-Jin,Lee, Tae-Suk,Nam, Keun-Soo,Kim, Keun-Jae
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p. 1389 - 1398
(2007/10/02)
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- MUSCARINIC RECEPTOR ANTAGONISTS
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A series of novel 3-phenyl-3-[1-(cyclicalkyl)pyrrolidin-3-yl] glutarimide derivatives have been prepared, including their pharmaceutically acceptable salts. The cyclic moiety present in these compounds is derived from either benzene or a heteroaryl such as benzofuran or 2,3-dihydrobenzofuran, or it is derived from an aromatic heterocyclic such as pyridine, pyrazine or thiophene, and it is attached to the adjacent alkyl group of the molecule by means of one of the available ring carbon atoms situated in the aromatic ring of the aforementioned cyclic ring moiety. These particular compounds are useful in therapy as selective muscarinic receptor antagonists, which are selective for smooth muscle muscarinic sites over cardiac muscarinic sites and therefore, are of value in the treatment of diseases associated with altered motility and/or smooth muscle tone as found in the gut, trachea and bladder. Methods for preparing these compounds from known starting materials are provided.
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- PYRROLIDINE DERIVATIVES
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Compounds of the formula STR1 wherein R, Y and R 1 are as defined in the specification. These compounds are muscarinic receptor antagonists which are selective for smooth muscle muscarinic sites over cardiac muscarinic sites, and are useful in the treatment of diseases associated with altered motility on tone of smooth muscle, including irritable bowel syndrome, diverticular disease, urinary incontinence, oesophageal achalasia and chronic obstructive airways disease.
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