Silver(I)-catalyzed annulation for the regioselective synthesis of N-imino-γ-carbolinium ylides from hydrazones of indole-3-carbonyl derivatives and propargylic alcohols.
نویسندگان
چکیده
A regioselective efficient synthetic approach to N-imino-γ-carbolinium ylides via AgOTf-catalyzed iminoannulation has been developed. This transformation proceeds via a silver(i) triflate-catalyzed consecutive Friedel-Crafts reaction/N-C bond formation sequence between the readily available indole derivatives and propargylic alcohols.
منابع مشابه
Copper-catalyzed tandem annulation/arylation for the synthesis of diindolylmethanes from propargylic alcohols.
Various highly substituted 2,3'-diindolylmethane heterocycles were prepared from propargylic alcohols and indole nucleophiles via a transition metal-catalyzed tandem indole annulation/arylation reaction for the first time. Among the metal catalysts we examined, the most economical copper(I) catalyst provided the highest efficiency. The indole nucleophiles could also be replaced by other electro...
متن کاملNaHSO4-SiO2: An Efficient Reusable Green Catalyst for Selective C-3 Propargylation of Indoles with Tertiary Propargylic Alcohols
Although several methods for the preparation of 4o propargyl indole derivatives have been published, this synthetic transformation is complicated by the tendency of 3o propargyl alcohols to form allenium intermediates in acidic media. It is therefore a challenge to find an efficient method for the C-3 propargylation of indoles with 3° propargylic alcohols. In this pa...
متن کاملAtom-Efficient Gold(I)-Chloride-Catalyzed Synthesis of α-Sulfenylated Carbonyl Compounds from Propargylic Alcohols and Aryl Thiols: Substrate Scope and Experimental and Theoretical Mechanistic Investigation
Gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols showed a wide substrate scope with respect to both propargylic alcohols and aryl thiols. Primary and secondary aromatic propargylic alcohols generated α-sulfenylated aldehydes and ketones in 60-97% yield. Secondary aliphatic propargylic alcohols generated α-sulfenylated ketones in...
متن کاملApplication of Poly(N, N′- dibromo-N-ethyl-naphthyl-2,7-disulfonamide) for the Regioselective Synthesis of New 3-Sulfenyl Indole Derivatives
Electron-rich aza-aromatic compounds such as indoles is structures of particular interest and importancein organic chemistry. A useful procedure for the preparation of new 3-sulfenyl indole derivatives using S-alkyl or S-arylthiophthalimides as sulfenylating agents and poly(N, N′-dibromo-N-ethyl-naphthyl-2,7-disulfonamide) as novel catalyst is described. The method represents an efficient prepa...
متن کاملSynthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: scope and computational studies.
Similar to propargylic carboxylates and sulphides, 3-propargylindoles undergo 1,2-indole migrations under cationic gold(I) catalysis. The intermediate Au-carbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moiety. Thus, 3-indenylindole derivatives were easily obtained through formal iso-Nazarov or Nazarov ...
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 12 47 شماره
صفحات -
تاریخ انتشار 2014