One-pot construction of fused polycyclic heteroarenes involving 7-azaindoles and α,β-unsaturated ketones.
نویسندگان
چکیده
A novel one-pot synthesis of π-conjugated polycyclic compounds, which could undergo further facile transformation to form complex polycyclic heteroarene compounds, has been realized between 7-azaindoles and α,β-unsaturated ketones. This distinctive cascade process proceeds via a rhodium(iii)-catalyzed alkylation/copper-catalyzed radical annulation-aromatization pathway.
منابع مشابه
Rapid access to α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile and the anti-proliferative activities of the products.
An effective and convenient method has been developed for the preparation of 2 or 2,4-substituted α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile in the presence of zinc dust, acetic acid and triethylamine. This protocol presents a simple, rapid and pot/step economical strategy for preparing biologically interesting α-carbolines with moderate...
متن کاملOne-Pot Synthesis of β,β-Disubstituted α,β-Unsaturated Carbonyl Compounds.
TiCl4-promoted aldol reaction of ketones as aldol acceptors followed by elimination of the titanoxy group from the Ti-aldolates affords β,β-disubstituted α,β-unsaturated carbonyl compounds in a one-pot procedure. The use of additives, such as DMF, N,N,N',N'-tetramethylethylenediamine, and pyridine, in the elimination step was found to be important.
متن کاملEnoyl acyl carrier protein reductase (FabI) catalyzed asymmetric reduction of the C=C double bond of α,β-unsaturated ketones: preparation of (R)-2-alkyl-cyclopentanones.
Enoyl-ACP reductase (FabI) was identified as a non-OYE 'ene'-reductase for asymmetric reduction of the C=C double bond of α, β-unsaturated ketones. Reduction of several 2-alkylidenecyclopentanones with A-FabI and E-FabI gave (R)-2-alkylcyclopentanones in 95-90% and 70-81% ee, respectively. The product ee was improved to 99-98% in high yield by subsequent one-pot biooxidation.
متن کاملInvestigation on the effect of trifluoromethyl group on the [3+2] cycloadditions of thiocarbonyl S-methanides with α, β-unsaturated ketones: A theoretical study using DFT
A [3+2] cycloaddition (32CA) reaction among a thiocarbonyl ylide (TCY 2) with (E)-4,4,4-trifluoro-4-phenylbut-3-en-2-one (TFB 4) as an electron-deficient enone in tetrahydrofuran (THF) were studied within the Molecular Electron Density Theory (MEDT), at the DFT-B3LYP/6-31G(d) computational level to analysis energetics, selectivities, and mechanistic aspects. The reaction can progress in four co...
متن کاملCopper-catalyzed cascade annulation of unsaturated α-bromocarbonyls with enynals: a facile access to ketones from aldehydes
A Cu-catalyzed cascade annulation of enynals with alkenyl or alkynyl a-bromocarbonyls for the synthesis of various cyclohexenone-fused polycyclic compounds is described. Up to six new C–C bonds and four new carbocycles can be established in a single reaction, highlighting the high efficiency and step-economics of this protocol. This reaction offers a novel and straightforward entry to the synth...
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 14 33 شماره
صفحات -
تاریخ انتشار 2016