19854-92-3Relevant articles and documents
Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: N-versus C-Attack Paths
Kardile, Rahul Dadabhau,Liu, Rai-Shung
supporting information, p. 8229 - 8233 (2020/11/03)
Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.
4-Methoxybenzyl (PMB), a versatile protecting group for the regiospecific lithiation and functionalization of pyrazoles
Subramanyam
, p. 761 - 774 (2007/10/02)
The use of 4-methoxybenzyl (PMB) protecting group for the regiospecific metallation/functionalisation of pyrazole is reported.
Carbodesilylation of (Trimethylsilyl)imidazoles and -pyrazoles
Effenberger, Franz,Roos, Michael,Ahmad, Roshan,Krebs, Andreas
, p. 1639 - 1650 (2007/10/02)
The preparation of the 1-methyl(trimethylsilyl) (TMS)-substituted imidazoles 3a, 4a, 8, 9, and 11a by silylation of the corresponding metallated imidazoles is described.Carbodesilylation of 3 with aldehydes or carboxylic halogenides occurs selectively in 2-position.In the presence of a strong base (CsF) the reactivity against carbon electrophiles correlates well with the stability of the imidazolyl anions; regioselective carbodesilylation in 2-, 5-, or 4-position of the twofold TMS-substituted imidazoles 3a and 9 therefore is possible, which allows the synthesis of a great variety of hydroxyalkyl-substituted imidazoles and of acylimidazoles.By using the dimethylsulfamoyl substituent as an N-protecting group, the N-unsubstituted 5-benzoylimidazole (26) as well as the comparable 5-benzoyl-pyrazole (30b) and 5-(hydroxyphenylmethyl)pyrazole (30a) are accessible. Key Words : Imidazoles, (trimethylsilyl)-, carbodesilylation of / Pyrazoles, (trimethylsilyl)-, carbodesilylation of / Carbodesilylation