4339-05-3Relevant articles and documents
Gold-Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration
Skaria, Manisha,More, Sayaji Arjun,Kuo, Tung-Chun,Cheng, Mu-Jeng,Liu, Rai-Shung
supporting information, p. 3600 - 3608 (2020/03/04)
This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured α-amino-2-en-1-ones and -1-als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)-nucleophilic additions on terminal alkynes, in contrast to a typical C(2)-route. For 3,3-dialkylprop-1-yn-3-ols, a methyl substituent is superior to long alkyl chains as the 1,2-migration groups toward α-imino gold carbenes. For secondary prop-1-yn-3-ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)-regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.
Alkynylation of aldehydes and ketones using the Bu4NOH/H 2O/DMSO catalytic composition: A wide-scope methodology
Schmidt, Elena Yu.,Cherimichkina, Natalia A.,Bidusenko, Ivan A.,Protzuk, Nadezhda I.,Trofimov, Boris A.
, p. 4663 - 4670 (2014/08/05)
The Favorsky reaction of a wide range of aldehydes and ketones with alkynes has been implemented under mild conditions (5-20 C). Using a Bu 4NOH/H2O/DMSO catalytic system, propargylic alcohols are formed cleanly in 39-93% (mostly 72-93%) yields and with ca. 100% selectivity. The method is suitable for aliphatic, aromatic, and heteroaromatic aldehydes and ketones, and for aliphatic, aromatic, and functionalized acetylenes. Thus, this represents the most general and efficient protocol to achieve the Favorsky reaction. Copyright
Anti-AIDS agents. Part 62: Anti-HIV activity of 2′-substituted 4-methyl-3′,4′-di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs
Zhang, Qian,Chen, Ying,Xia, Peng,Xia, Yi,Yang, Zheng-Yu,Yu, Donglei,Morris-Natschke, Susan L.,Lee, Kuo-Hsiung
, p. 5855 - 5857 (2007/10/03)
Four 4-methyl-3′,4′-di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs (7a-d) with different alkyl substituents at the 2′-position were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 2′-Methyl-2′-ethyl-4-methyl DCK (7b) was more potent (EC50 = 0.22 μM, TI > 175) than the other three compounds (7a, 7c, and 7d), but significantly less potent than 4-methyl DCK (2, EC50 = 0.0059 μM, TI > 6600). Four 4-methyl-3′,4′- di-O-(-)-camphanoyl-(+)-cis-khellactone (4-methyl DCK) analogs (7a-d) with different alkyl substituents at the 2′-position were synthesized and evaluated for inhibition of HIV-1 replication in H9 lymphocytes. 2′-Methyl-2′-ethyl-4-methyl DCK (7b) was more potent (EC 50 = 0.22 μM, TI > 175) than the other three compounds (7a, 7c, and 7d), but significantly less potent than 4-methyl DCK (2, EC50 = 0.0059 μM, TI > 6600). The bioassay results indicated that the 2′-substituents had a strong effect on the anti-HIV activity, and gem-dimethyl substitution at the 2′-position was greatly preferable to larger alkyl substituents or hydrogen atoms.