Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines.
نویسندگان
چکیده
Various tetrasubstituted pyrroles/pyrazoles have been prepared from nitro-substituted 1,3-enynes with aromatic amines/hydrazines via a copper-catalyzed cascade aza-Michael addition, cyclization and aromatization at room temperature. This protocol is also effective for the synthesis of tetrasubstituted pyrazoles in high yields.
منابع مشابه
Selective synthesis of functionalized pyrroles from 3-aza-1,5-enynes.
2-Trifluoromethyl-5-(arylsulfonyl)methyl pyrroles and 2-trifluoromethyl-4-(arylsulfonyl)methyl pyrroles were selectively synthesized from trifluoromethyl-substituted 3-aza-1,5-enynes via a cyclization/sulfonyl group migration cascade catalyzed by AgOOCCF3 and CsOPiv, respectively. Alkylvinyl-substituted pyrroles were generated from seven-atom skeleton 3-aza-1,5-enynes via aryl sulfinic acid eli...
متن کاملSynthesis of Substituted 2-Amino-1,3-oxazoles via Copper-Catalyzed Oxidative Cyclization of Enamines and N,N-Dialkyl Formamides.
A facile synthesis of 2-amino-1,3-oxazoles via CuI -catalyzed oxidative cyclization of enamines and N,N-dialkyl formamides has been developed. The reaction proceeds through an oxidative C-N bond formation, followed by an intramolecular C(sp2 )-H bond functionalization/C-O cyclization in one pot. This protocol provides direct access to useful 2-amino-1,3-oxazoles and features protecting-group-fr...
متن کاملOne-pot Synthesis of Pyrono [2,3] Quinoline via the Tandem Cyclization of Algar-Flyn-Oyamanda Reactions
A new and imaginative technique for the synthesis of substituted pyranoquinoline via Algar Flyn Oyamanda oxidation cyclization approach has been achieved by hydrogen peroxide and sodium hydroxide catalyzed of quinoline chalcone with intramolecular cyclization to formed pyranoquinoline. In this reaction, two new C-C bonds were formed in a one step with high atom economy. The possible reaction pa...
متن کاملTandem Synthesis of 2,3,4,5-Tetrasubstituted Pyrroles from Aromatic Aldehydes Using Diethylene Glycol-bis(3-methylimidazolium) Dihydroxide as an Efficient Catalyst
A sequential process strategy was introduced for the synthesis of 2,3,4,5-tetrasubstituted pyrroles by the formation of benzoin from the corresponding aromatic aldehyde and followed by condensation reaction with 1,3-dicarbonyl compounds and ammonium acetate in the presence of diethylene glycol-bis(3-methylimidazolium) dihydroxide as catalyst in refluxing ethanol. The recycled catalyst could be ...
متن کاملPalladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes: facile synthesis of bicyclo[4.1.0]heptan-5-ones.
We here describe a new palladium-catalyzed oxidative 6-exo-trig cyclization of 1,6-enynes at room temperature using tBuONO as an oxidant for the synthesis of 3-bicyclo[4.1.0]heptan-5-ones. This cascade strategy involves the hydration, cyclization and cyclopropanation sequence, and represents a new transition-metal-catalyzed oxidative cyclization of 1,6-enynes in a 6-exo-trig fashion.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic & biomolecular chemistry
دوره 13 9 شماره
صفحات -
تاریخ انتشار 2015