A new rapid multicomponent domino heteroannulation of heterocyclic ketene aminals: solvent-free regioselective synthesis of functionalized benzo[g]imidazo[1,2-a]quinolinediones.
نویسندگان
چکیده
A highly efficient and straightforward three-component cascade reaction was developed to synthesize benzo[g]imidazo[1,2-a]quinolinedione derivatives from heterocyclic ketene aminals (HKAs), aldehydes, and 2-hydroxy-1,4-naphthoquinone (HNQ) via Et(3)N-catalyzed tandem [3 + 2 + 1] annulation under solvent-free conditions. The reactions were very mild, convenient and highly regioselective to form new fused tetracyclic target molecules.
منابع مشابه
Four-component cascade heteroannulation of heterocyclic ketene aminals: synthesis of functionalized tetrahydroimidazo[1,2-a]pyridine derivatives.
An efficient and straightforward four-component synthetic protocol has been developed to synthesize imidazo[1,2-a]pyridines and imidazo[1,2,3-ij][1,8]naphthyridine derivatives incorporating medicinally privileged heterosystems from heterocyclic ketene aminals, aldehydes, diketene, and amines via cascade reactions, including diketene ring-opening, Knoevenagel condensation, aza-ene reaction, imin...
متن کاملChemistry of heterocyclic ketene aminals: construction of imidazo(pyrido)[1,2-a]pyridines and imidazo(pyrido)[3,2,1-ij][1,8]naphthyridines via DABCO-catalyzed tandem annulations.
2-(2-Chloroaroyl)methyleneimidazolidines with four reactive sites show fascinating structural features and could be used as a new strategy for the synthesis of novel heterocycles. This paper presents our new findings in the reaction of 2-(2-chloroaroyl)methyleneimidazolidines with allenic esters affording functionalized imidazo(pyrido)[1,2-a]pyridines via DABCO-catalyzed tandem annulations. Of ...
متن کاملA new rapid multicomponent domino reaction for the formation of functionalized benzo[h]pyrazolo[3,4-b]quinolines.
A new multicomponent domino reaction for rapid and regioselective synthesis of highly functionalized benzo[h]pyrazolo[3,4-b]quinolines has been established. The reaction can be conducted by using readily available and inexpensive substrates under microwave irradiation within short periods of 10-26 min. Good to excellent chemical yields (61-91%) and complete regioselectivity have been achieved f...
متن کاملA Green Multicomponent One-pot Synthesis of 9, 10-Diaryl-7H-benzo[d,e]imidazo[2,1-a]isoquinolin-7-one Derivatives using Nanoporous Base Silica (SBA-Pr-NH2) as Catalyst
Organic-inorganic hybrid mesoporous materials such as amino functionalized silica (SBA-Pr-NH2) have received considerable attention due to their basic catalytic applications and adsorption functions. In this work, we investigated the efficient role of SBA-Pr-NH2 as a heterogeneous nano catalyst in the synthesis of 9,10-diaryl-7H-benzo[d,e]imidazo[2,1-a]isoquinolin-7-one derivatives. Application...
متن کاملIndium chloride (InCl3) catalysed domino protocol for the regioselective synthesis of highly functionalized pyranopyrazoles under mild conditions
Regioselective synthesis of highly functionalized pyranopyrazoles was achieved in excellent yield from phenyl pyrazolone, substituted aromatic aldehyde with nitroketene-N,S-acetal in the presence of indium trichloride as a versatile catalyst under reflux condition in ethanol-water mixture. All reactions preceeded within a short period of time with excellent purity. All of the synthesized compou...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Organic & biomolecular chemistry
دوره 11 5 شماره
صفحات -
تاریخ انتشار 2013