- I2-Mediated oxidative bicyclization of 4-pentenamines to prolinol carbamates with CO2 incorporating oxyamination of the C=C bond
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A metal-free oxyamination reaction of alkenes with ambient CO2 is reported. In the presence of I2 and DBU, CO2 is applied in situ as a protecting group to regulate the nucleophilicity of the amino group and facilitate the bicyclization of 4-pentenamines with high chemoselectivity. Moreover, this reaction provided a feasible approach to prepare prolinol carbamates with good tolerance of functional groups and high efficiency under mild conditions.
- Wang, Sheng,Zhang, Xiaowei,Cao, Chengyao,Chen, Chao,Xi, Chanjuan
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supporting information
p. 4515 - 4519
(2017/10/13)
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- D1-like receptors distinguishing thieno-azecine regioisomers
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Designing ligands with D1/D5 subtype selectivity is a challenge because of the high identity within the receptor helices. Based on the lead compounds 1-3, the thieno-benzazecine regioisomers 4 and 5 were synthesized and biologically evaluated for their affinity towards the five dopamine receptor subtypes utilizing a radioligand binding affinity technique. Within the D1-like family, compound 4 showed 20 fold selectivity for the D5 subtype over D1 subtype (Ki = 3 nM, D1: 60 nM), while its regioisomer, compound 5 with a reversed thiophene position, prefers the D1 subtype over the D5 subtype (Ki = 4 nM, D5: 15 nM). The benzothieno-benzazecine analog 6 was shown to be one of the few azecine derivatives with high affinity for both the D1- and the D2-like family members in the same order of magnitude (Ki = 1.5 nM for D2 and 1.9 nM for D5). Thorough analysis of the amino acid residues constituting the binding pockets of the target dopamine receptor subtypes revealed that at the D5 receptor, either serine S 6.62 and threonine T 7.33 residues or a water network, stabilized by anionic amino acids could contribute to the selectivity pattern of the synthesized compounds.
- Abdel-Fattah, Mohamed A. O.,Abadi, Ashraf H.,Lehmann, Jochen,Schweikert, Peter M.,Enzensperger, Christoph
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p. 1679 - 1686
(2015/09/21)
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- The Concise Synthesis of Unsymmetric Triarylacetonitriles via Pd-Catalyzed Sequential Arylation: A New Synthetic Approach to Tri- and Tetraarylmethanes
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The selective synthesis of multiarylated acetonitriles via sequential palladium-catalyzed arylations of chloroacetonitrile is reported. The three aryl groups are installed via a Pd-catalyzed Suzuki-Miyaura cross coupling reaction followed by back-to-back C-H arylations to afford triarylacetonitriles in three steps with no over-arylation at any step. The triarylacetonitrile products can be converted into highly functionalized species including tetraarylmethanes. This new strategy provides rapid access to a variety of unsymmetrical tri- and tetraarylmethane derivatives from simple, readily available starting materials. (Chemical Presented)
- Nambo, Masakazu,Yar, Muhammad,Smith, Joel D.,Crudden, Cathleen M.
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supporting information
p. 50 - 53
(2015/07/28)
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- Intramolecular PdII-catalyzed dehydrogenative C(sp 3)-C(sp2) coupling: An alternative to Pd 0-catalyzed C(sp3)-H arylation from aryl halides?
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The synthesis of fused thiophene-cyclopentanes by PdII-catalyzed dehydrogenative C(sp2)-H/C(sp3)-H coupling is described. This reaction shows interesting chemo- and diastereoselectivity, however a direct comparison showed that it is yet much less efficient than the two-step sequence composed of electrophilic halogenation and Pd0-catalyzed C(sp3)-H arylation.
- Pierre, Cathleen,Baudoin, Olivier
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p. 4473 - 4478
(2013/06/26)
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- Synthesis of α-Aryl nitriles through palladium-catalyzed decarboxylative coupling of cyanoacetate salts with aryl halides and triflates
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Worth its salt: The palladium-catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono- and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α-aryl nitriles and has good functional group tolerance. S-Phos=2-(2,6- dimethoxybiphenyl)dicyclohexylphosphine), Xant-Phos=4,5-bis(diphenylphosphino)- 9,9-dimethylxanthene. Copyright
- Shang, Rui,Ji, Dong-Sheng,Chu, Ling,Fu, Yao,Liu, Lei
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supporting information; experimental part
p. 4470 - 4474
(2011/06/24)
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- SPIROCYCLIC CYCLOHEXANE DERIVATIVES WITH AFFINITY FOR THE ORL1-RECEPTOR
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The invention relates to spirocyclic cyclohexane derivatives, to a method for the production thereof, to medicaments containing said compounds and to the use of spirocyclic cyclohexane derivatives for the production of medicaments.
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Page/Page column 32
(2008/06/13)
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- SYNTHESE D'OXADIAZOLES ET D'OXAZOLES THIOPHENIQUES
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Some potentially active drugs: oxadiazoles (4, 8, 17), oxazoles (10, 12a, 12b, 13) heterocycles substituted by a thiophenic moiety have been prepared by a multistep procedure. Key words: Thiophene; oxadiazole; oxazole; potentially active drugs.
- Oussaid, Boualem,Moeini, Leila,Garrigues, Bernard,Villemin, Didier
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