5415-80-5Relevant academic research and scientific papers
Base-controlled chemoselectivity: direct coupling of alcohols and acetonitriles to synthesise α-alkylated arylacetonitriles or acetamides
Bai, Liang,Ge, Min-Tong,Li, Chen,Qiu, Yuan-Rui,Wang, Ying,Xia, Ai-Bao,Xu, Dan-Qian
supporting information, p. 15200 - 15204 (2021/09/06)
We achieved chemoselective synthesis of α-alkylated arylacetonitriles and acetamides by combining Ir complex-catalysed direct coupling of alcohols and nitriles by a simple adjustment of the base. Methanol and ethanol performed well as the alkylating reagents. This method of acetonitrile alkylation provided a novel approach for carbon chain extension.
Nickel-catalyzed hydrogen-borrowing strategy: Chemo-selective alkylation of nitriles with alcohols
Banerjee, Debasis,Bera, Atanu,Bera, Sourajit
supporting information, p. 6850 - 6853 (2020/07/04)
The first nickel-catalyzed hydrogen-borrowing alkylation of a series of aryl acetonitriles with a variety of aryl, heteroaryl, allylic and alkyl alcohols releasing water as the by-product (>33 examples, up to 90% yield) is reported.
Reductive C?C Coupling from α,β-Unsaturated Nitriles by Intercepting Keteniminates
Hale, Lillian V. A.,Sikes, N. Marianne,Szymczak, Nathaniel K.
supporting information, p. 8531 - 8535 (2019/05/21)
We present an atom-economic strategy to catalytically generate and intercept nitrile anion equivalents using hydrogen transfer catalysis. Addition of α,β-unsaturated nitriles to a pincer-based Ru?H complex affords structurally characterized κ-N-coordinated keteniminates by selective 1,4-hydride transfer. When generated in situ under catalytic hydrogenation conditions, electrophilic addition to the keteniminate was achieved using anhydrides to provide α-cyanoacetates in high yields. This work represents a new application of hydrogen transfer catalysis using α,β-unsaturated nitriles for reductive C?C coupling reactions.
Pyrroloisoquinoline antidepressants. 2. In-depth exploration of structure-activity relationships
Maryanoff,McComsey,Gardocki,Shank,Costanzo,Nortey,Schneider,Setler
, p. 1433 - 1454 (2007/10/02)
A series of pyrrolo[2,1-a]isoquinolines, and related compounds, were examined for antidepressant-like activity, by virtue of their antagonism of tetrabenazine-induced ptosis and sedation, and inhibition of biogenic amine uptake. Thus, we have identified some of the most potent antagonists of TBZ-induced ptosis and some of the most potent inhibitors of the uptake of dopamine, norepinephrine, and serotonin (in rat brain synaptosomes) ever reported. Compounds of particular note, in this regard, are 52b, 29b, 22b, and 48b, respectively. Biological activity was chiefly manifested by the trans isomeric class. Also, through resolution of four compounds, 7b, 24b, 37b, and 48b, biological activity was found to be associated with the (+) enantiomer subgroup (salts measured at 589 nm in MeOH), corresponding to the 6S,10bR absolute configuration for 7b, 37b, and 48b, and the 6R,10bR configuration for 24b. An X-ray determination on (+)-24b·HBr established its absolute configuration; configurations for the other compounds were verified by enantiospecific synthesis starting with (+)-(R)-2-phenylpyrrolidine. Regarding the pendant phenyl ring, diverse substitution patterns were investigated. Those substitutions that were particularly unfavorable were 3',4',5'-trimethoxy (20b), 2',3',4',5',6'-pentafluoro (34b), 2'-trifluoromethyl (38b), 3',5'-bis(trifluoromethyl) (42b), 4'-n-butyl (44b), 2'-cyano (47b), 4'-methylsulfonyl (50b), and 2'-carboxy (58b). Exceedingly potent compounds, in one way or another, were 10b-12b, 22b, 23b, 25b, 28b, 29b, 33b, 45b, 48b, 51b-53b. The pattern of aromatic substitution had a strong impact on selectivity in the uptake tests (NE vs. DA vs. 5-HT). Activity was significantly diminished by methyl substitution of 7b at the 5 (65, 66), 6 (61b), or 10b (60b) position, by changing the phenyl group of 7b to cyclohexyl (67b), benzyl (68b), or H (72), by moving the phenyl group of 7b to the 5 (69) or 10b (70) position, by expansion of ring B to an azepine (78b), and by modification of ring C to an azetidine (77b), piperidine (75b), or azepine (74b). The interaction of selected analogues with various CNS receptors is reported. Little affinity was shown for the muscarinic cholinergic receptor, suggesting a lack of anticholinergic side effects. Interestingly, 24b and 33b displayed a high affinity for the serotonin-2 receptor, analogous to mianserin and clomipramine. After the body of data was reviewed, derivatives 24b and 48b were chosen for advanced development.
Polycyclic amines and intermediates therefor
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, (2008/06/13)
This invention relates to a new method for the preparation of amines containing alkylene groups by using cyclic alkylene sulphuric esters, and novel intermediates for use in the method. The new method is useful for preparation of i.a. pharmaceuticals. The novel intermediates are useful i.a. as surfactants.
Possible Antihypertensive Agents: Syntheses of N-Aralkyl-β-substituted Phenylethylamines and N-Alkyl/acyl-6,7-dimethoxy-1--1,2,3,4-tetrahydroisoquinolines
Kansal, V. K.,Bhaduri, A. P.
, p. 885 - 890 (2007/10/02)
Syntheses of a number of N-arylalkyl-β-phenylethylamines and N-alkyl/acyl-6,7-dimethoxy-1--1,2,3,4-tetrahydroisoquinolines along with the results of antihypertensive screening in experimental animals have been described.
