Continuous-flow synthesis of 3,5-disubstituted pyrazoles via sequential alkyne homocoupling and Cope-type hydroamination
نویسندگان
چکیده
منابع مشابه
Synthesis of 3,5-disubstituted pyrazoles via Cope-type hydroamination of 1,3-dialkynes.
An efficient method for the synthesis of 3,5-disubstituted pyrazoles is described. The reactions of 1,3-dialkynes with hydrazine proceeded smoothly in dimethyl sulfoxide under mild reaction conditions to produce 3,5-disubstituted pyrazoles in satisfactory to excellent yields. A one-pot procedure of the transformation has been developed.
متن کاملContinuous flow synthesis of a carbon-based molecular cage macrocycle via a three-fold homocoupling reaction.
The facile synthesis of the cage molecule (C110H56Br2) via a remarkable three-fold homo-coupling macrocyclization reaction using continuous flow methodology is reported. Synthesis via continuous flow chemistry improves the residence time, safety, and environmental profile of this synthetically challenging reaction. Further, the new cage possesses halogen atoms at its apex that serve to expand t...
متن کاملSynthesis of 3,3-disubstituted-2,3-dihydroazanaphthoquinones via simultaneous alkyne oxidation and nitrile hydration of ortho-alkynylarenenitriles.
o-Alkynylarenenitriles when heated with Pd(OAc)2/H2O/(±)-CSA in DMSO undergo simultaneous alkyne oxidation and nitrile hydration to give 3-aryl-3-hydroxy-2,3-dihydroazanaphthoquinones. Upon treatment with (±)-CSA, these compounds form 3-arylazanaphthoquinones in situ, which add to electron-rich aromatics and terminal alkene/alkyne to afford 3,3-disubstituted-2,3-dihydroazanaphthoquinones.
متن کاملIntermolecular Cope-type hydroamination of alkynes using hydrazines.
Metal-free, intermolecular hydroaminations are performed upon heating aryl acetylenes and MeNHNH(2) at 140 degrees C, with preferential formation of the linear, "anti-Markovnikov" hydrazones.
متن کاملImproved Cope-type hydroamination reactivity of hydrazine derivatives.
A systematic investigation on the metal-free, Cope-type hydroamination reactivity of hydrazides and analogues is reported. Optimization of the hydrazide structure resulted in more facile intramolecular reactivity and enabled intermolecular reactions of alkenes, thus providing a direct approach to polysubstituted hydrazides.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: RSC Advances
سال: 2019
ISSN: 2046-2069
DOI: 10.1039/c9ra01590f