Indium(III) chloride catalyzed highly diastereoselective domino synthesis of indenodithiepines and indenodithiocines.
نویسندگان
چکیده
An atom-economical diastereoselective synthesis of indenodithiepines and indenodithiocines has been developed via a domino reaction of propargylic alcohols and dithioacetals in the presence of InCl3 as a catalyst. A range of functionalized dithiepines and dithiocines, fused to the indene ring, were obtained in good to excellent yields under mild conditions.
منابع مشابه
Indium 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 کاملAn iodine catalyzed metal free domino process for the stereoselective synthesis of oxygen bridged bicyclic ethers.
A domino reaction has been developed for the synthesis of oxygen bridged bicyclic ethers through the coupling of 4-(2-hydroxyethyl)cyclohex-3-enols with aldehydes in the presence of 10 mol% of molecular iodine in dichloromethane at 25 °C. This method is highly diastereoselective affording the corresponding bicyclic ethers, i.e. octahydro-4a,7-epoxyisochromenes in good yields with high selectivi...
متن کاملAn efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium-catalyzed multi-component domino reaction
Various novel pyrano [2,3-d]pyrimidines 5 and furopyrano [2,3-d]pyrimidines 7 were synthesized in 80-99% yields via a multicomponent domino Knoevenagel/hetero-Diels-Alder reaction of 1,3-dimethyl barbituric acid with an aromatic aldehyde and ethyl vinyl ether/2,3-dihydrofuran in presence of 1 mol% of indium(III) chloride. The reaction also proceeds in aqueous media without using any catalyst, b...
متن کاملA Convenient Base-Mediated Diastereoselective Synthesis of 2-Oxo-N,4,6-triarylcyclohex-3-enecarboxamides via Claisen-Schmidt Condensation
Sodium acetate catalyzed the multi-component reaction of acetophenone, aromatic aldehydes, and acetoacetanilide in the water-ethanol mixture (1:1) at ambient temperature via Claisen-Schmidt condensation results in the formation of highly substituted cyclohexenones in 89–98% yields. The developed efficient catalytic approach to the substituted cyclohexenones – the promising ...
متن کاملA simple, solvent-free four-component domino synthesis of 1H-pyrazolo [1, 2-b] phthalazine-5, 10-dione derivatives catalyzed by copper (II) oxide
An eco-safe and facile multi-component domino reaction has been described for the synthesis of 1H-pyrazolo [1, 2-b] phthalazine-5, 10-dione derivatives. The products were obtained by a four-component condensation reaction between phthalimide, hydrazine monohydrate, aromatic aldehyde derivatives and malononitrile in the presence of a catalytic amount of copper (II) oxide (CuO) ...
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:
- Chemical communications
دوره 51 4 شماره
صفحات -
تاریخ انتشار 2015