Acetal-initiated Prins bicyclization for the synthesis of hexahydrofuro-[3,4-c]furan lignans and octahydropyrano[3,4-c]pyran derivatives.
نویسندگان
چکیده
An acetal-initiated Prins bicyclization approach has been developed for the stereoselective synthesis of hexahydrofuro[3,4-c]furan lignans. This also provides a direct way to generate a new series of octahydropyrano[3,4-c]pyran derivatives in a single-step process.
منابع مشابه
A novel domino cyclization for the stereoselective synthesis of indeno[2,1-c]pyran and cyclopenta[c]pyran derivatives.
A novel bicyclization of 2-(2-(hydroxymethyl)-1-methylene-2,3-dihydro-1H-inden-2-yl)ethanol with aldehydes in the presence of 10 mol% BF3·OEt2 in dichloromethane at 0-25 °C affords the biologically relevant indeno[2,1-c]pyran scaffolds in good yields with high selectivity. Similarly the bicyclization of 2-(1-(hydroxymethyl)-2-methylenecyclopentyl)ethanol with aldehydes generates the correspondi...
متن کاملLactic acid-catalyzed Eco-friendly Cyclization Reaction for the Synthesis of 4H-benzo[b]pyrans and 3,4-dihydropyrano[c]chromenes in EtOH/H2O as an Efficient Green Reaction Medium
An environmentally friendly, green, and highly efficient process for the synthesis of biologically and pharmacologically 4H-benzo[b]pyrans and 3,4-dihydropyrano [c] chromenes is developed by condensing cyclic aromatic aldehydes, malononitrile, and dimedone or 4‐hydroxycoumarin in the presence of lactic acid as an efficient and green catalyst. The corresponding products have b...
متن کاملFour-Component Bicyclization Approaches to Skeletally Diverse Pyrazolo[3,4-b]pyridine Derivatives
A novel four-component bicyclization strategy has been established, allowing a flexible and practical approach to 37 examples of multicyclic pyrazolo[3,4-b]pyridines from low-cost and readily accessible arylglyoxals, pyrazol-5-amines, aromatic amines, 4-hydroxy-6-methyl-2H-pyran-2-one, and cyclohexane-1,3-diones. The polysubstituted cyclopenta[d]pyrazolo[3,4-b]pyridines were stereoselectively s...
متن کاملSynthesis of 3,4-Dihydroquinoxalin-2-Amine, Diazepine-Tetrazole and Benzodiazepine-2-Carboxamide Derivatives with the Aid of H6P2W18O62/Pyridino-Fe3O4
In the current study, a magnetic inorganic–organic nanohybrid material (HPA/TPI-Fe3O4) was produced and used as an efficient, highly recyclable and eco-friendly catalyst for the one-pot and multicomponent synthesis of 3,4-dihydroquinoxalin-2-amine, diazepine-tetrazole and benzodiazepine-2-carboxamide derivatives with high yields and in a short range of time (20–35 min)...
متن کاملSynthesis of 3,4-Dihydropyrano[c]Chromene Derivatives Using Sulfonic Acid Functionalized Silica (SiO2PrSO3H)
3,4-ِDihydropyrano[c]chromene derivatives were synthesized using sulfonic acid functionalized silica (SiO2-Pr-SO3H) as a highly efficient heterogenous solid acid catalyst via one-pot three-component condensation of aromatic aldehydes with malononitrile and 4-hydroxycoumarin in excellent yields.
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 12 26 شماره
صفحات -
تاریخ انتشار 2014