Isothiourea-mediated one-pot synthesis of trifluoromethyl substituted 2-pyrones.
نویسندگان
چکیده
A one-pot isothiourea-mediated Michael addition/lactonization/thiol elimination cascade sequence for the formation of 4,6-disubstituted and 3,4,6-trisubstituted 2-pyrones from (phenylthio)acetic acids and α,β-unsaturated trifluoromethyl ketones is described. The synthesis of a COX-2 inhibitor and the wide-ranging derivatization of the 2-pyrone moiety to trifluoromethyl substituted aromatics and heteroaromatics is also disclosed.
منابع مشابه
Isothiourea-Mediated One-Pot Synthesis of Functionalized Pyridines**
Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/lactamization, thiophenol elimination, and N- to O-sulfonyl migration, giving 2-sulfonate-substituted pyridines which are readily derivatized to generate structural diversity.
متن کاملLewis Base Directed Cycloaddition Reactions of 2-Pyrones and Alkynylaluminum Reagents
In situ generated alkynylaluminum reagents have been utilized in a [4 + 2] cycloaddition with 2-pyrones bearing a Lewis basic donor. The reactions proceed at or below room temperature and with complete regiocontrol. This one-pot method affords diversely substituted aromatic compounds under very mild conditions.
متن کاملOne-Pot solvent-free synthesis of Highly Substituted Imidazoles catalyzed by zeolite
A series of tri- and tetra- substituted imidazoles were synthesized from benzyl, aldehyde and ammonium acetate in the presence of zeolite as an ecofriendly reusable catalyst under microwave irradiation in the absence of solvent. The yields are high to excellent and the use of microwave irradiation reduces reaction times to few minute.
متن کاملUrea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
متن کاملUrea-hydrogen peroxide/silica phosphoric acid-catalyzed oxidation- condensation Tandem reaction: One-pot synthesis of 2-substituted benzimidazoles from alcohols
An efficient one-pot oxidation/condensation tandem process has been developed for the synthesis of 2-substituted benzimidazole derivatives from benzylic alcohols and 1,2-phenylenediamine with use of urea-hydrogen peroxide/silica phosphoric acid as a bifunctional catalyst. This method provides a rapid and efficient access to 2-substituted benzimidazoles.
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 letters
دوره 16 3 شماره
صفحات -
تاریخ انتشار 2014