- Synthesis of 1,2-Dihydro-Substituted Aniline Analogues Involving N -Phenyl-3-aza-Cope Rearrangement Using a Metal-Free Catalytic Approach
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An efficient metal-free domino reaction leading to structural/electronically divergent 1,2-dihydropyridines from easily accessible propargyl vinyl anilines via N-phenyl 3-aza-Cope sigmatropic rearrangement is reported with good to excellent yields using 1,2-dichlorobenzene as solvent under thermal conditions. Spirocyclic substitution is also tolerated under the present optimized conditions.
- Alduhaish, Osamah,Varala, Ravi,Adil, Syed Farooq,Khan, Mujeeb,Siddiqui, Mohammed Rafiq H.,Alwarthan, Abdulrhman,Alam, M. Mujahid
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- Superbase-Promoted Addition of Acetylene Gas to the C=N Bond
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A new Csp3–Csp bond forming reaction is reported: the C=N bond of widespread imines reacts with acetylene gas in the presence of superbase KOtBu/DMSO at room temperature to afford terminal α-aminoacetylenes in up to 94 % yield. The reaction all
- Schmidt, Elena Yu.,Bidusenko, Ivan A.,Protsuk, Nadezhda I.,Demyanov, Yan V.,Ushakov, Igor A.,Trofimov, Boris A.
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p. 5875 - 5881
(2019/09/10)
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- A convenient method for the aromatic amino-claisen rearrangement of N-(1,1-disubstituted-allyl)anilines
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N-(1,1-Disubstituted-allyl)anilines are rearranged cleanly and in high yield to 2-(3,3-disubstituted-allyl)anilines using a catalytic amount of p-toluenesulfonic acid in acetonitrile/water (10:1).
- Cooper,Lucas,Taylor,Ward,Williamson
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p. 621 - 625
(2007/10/03)
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- Synthesis and biological activity of a novel series of nonsteroidal, peripherally selective androgen receptor antagonists derived from 1,2- dihydropyridono[5,6-g]quinolines
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A new nonsteroidal antiandrogenic pharmacophore has been discovered using cell-based cotransfection assays with human androgen receptor (hAR). This series of AR antagonists is structurally characterized by a linear tricyclic 1,2-dihydropyridono[5,6-g]quinoline core. Analogues inhibit AR- mediated reporter gene expression and bind to AR as potently as or better than any known AR antagonists. Several analogues also showed excellent in vivo activity in classic rodent models of AR antagonism, inhibiting growth of rat ventral prostate and seminal vesicles, without accompanying increases in serum gonadotropin and testosterone levels, as is seen with other AR antagonists. Investigations of structure - activity relationships surrounding this pharmacophore resulted in molecules with complete specificity for AR, antagonist activity on an AR mutant commonly observed in prostate cancer patients, and improved in vivo efficacy. Molecules based on this series of compounds have the potential to provide unique and effective clinical opportunities for treatment of prostate cancer and other androgen-dependent diseases.
- Hamann, Lawrence G.,Higuchi, Robert I.,Zhi, Lin,Edwards, James P.,Wang, Xiao-Ning,Marschke, Keith B.,Kong, James W.,Farmer, Luc J.,Jones, Todd K.
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p. 623 - 639
(2007/10/03)
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- REACTIONS OF NITROGEN NUCLEOPHILES WITH 1-BROMOALLENES: REGIOSELECTIVE SYNTHESIS OF PROPARGYLAMINES
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The results of a study on the reactivity of 3-alkyl- and 3,3-dialkyl-1-bromo-1,2-dienes 2 towards nitrogen nucleophiles, such as aqueous ammonia, lithium amide, aliphatic and aromatic amines allowed us to propose new methods for the synthesis of propargylamines, 1, with an available acetylenic hydrogen.The regio- and the stereoselectivity of these reactions are examined and possible mechanisms are discussed.
- Geri, Roberto,Polizzi, Carmela,Lardicci, Luciano,Caporusso, Anna Maria
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p. 241 - 248
(2007/10/02)
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- Copper Catalyzed Aminolysis of Bromoallenes as a New Efficient Route to Propargylamines
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An efficient procedure of general applicability for the synthesis of secondary and tertiary propargylamines by copper mediated aminolysis of 1-bromo-1,2-dienes is described.Key Words: propargylamines; bromoallenes; aminolysis; regioselectivity; Cu promote
- Caporusso, Anna Maria,Geri, Roberto,Polizzi, Carmela,Lardicci, Luciano
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p. 7471 - 7472
(2007/10/02)
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