A direct preparation of N-unsubstituted pyrrole-2,5-dicarboxylates from 2-azidocarboxylic esters.
نویسنده
چکیده
A new and easy method for synthesis of symmetric pyrrole-2,5-dicarboxylate derivatives via a simple titanium(IV)-mediated oxidative dimerization of 2-azidocarboxylic esters is described. The process involves a transformation of titanium(IV) enolates into nonisolated 2-iminoesters, which undergo an oxidative coupling and ring closure to give the aromatic pyrrole system. A mechanism, scope and limitations of the new method are discussed.
منابع مشابه
Synthesis of novel 5-alkyl/aryl/heteroaryl substituted diethyl 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates by aziridine ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters
A novel synthetic methodology has been developed for the synthesis of diethyl 5-alkyl/aryl/heteroaryl substituted 3,4-dihydro-2H-pyrrole-4,4-dicarboxylates (also called 2-substituted pyrroline-4,5-dihydro-3,3-dicarboxylic acid diethyl esters) by iodide ion induced ring expansion of 2-[(aziridin-1-yl)-1-alkyl/aryl/heteroaryl-methylene]malonic acid diethyl esters in very good to excellent yields ...
متن کاملCarbon catalyst derived from Himalayan pine for the C-N coupling of organic molecules leading to pyrrole formation
Carbon catalyst consisting of a hybrid structure made up of amorphous carbon and nanographite was prepared from the leaves of Pinus Roxburghii. The catalyst was prepared through sodium hydroxide and hydrochloric acid treatment of the dried pine leaves; and further functionalized with sulfuric acid treatment to incorporate the acidic functionalities. The synthesized catalyst was characterized by...
متن کامل5-Hydroxyalkyl derivatives of tert-butyl 2-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate: diastereoselectivity of the Mukaiyama crossed-aldol-type reaction.
The title compounds, rac-(1'R,2R)-tert-butyl 2-(1'-hydroxyethyl)-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate, C(17)H(20)N(2)O(6), (I), rac-(1'S,2R)-tert-butyl 2-[1'-hydroxy-3'-(methoxycarbonyl)propyl]-3-(2-nitrophenyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylate, C(20)H(24)N(2)O(8), (II), and rac-(1'S,2R)-tert-butyl 2-(4'-bromo-1'-hydroxybutyl)-5-oxo-2,5-dihydro-1H-pyrrole-1-car...
متن کاملSynthesis of Pyrrole Phosphonate Esters: Emphasis on Pyrrole NH Acids and Dialkylacetylenic Esters Substitution
Reaction of dialkyl acetylenedicarboxylates 1a-c andpyrrole derivatives 2a-e in the presence of triphenylphosphite (TPP) was investigated and the effect of the pyrrole substitution was established. Diastereoselectivity is observed with pyrroles, 2a,b, yieldingphosphonate ester derivatives 3a-f and 4,and their relative configuration is determined by 1H/13C and 31</...
متن کاملCarbon catalyst derived from Himalayan pine for the C-N coupling of organic molecules leading to pyrrole formation
Carbon catalyst consisting of a hybrid structure made up of amorphous carbon and nanographite was prepared from the leaves of Pinus Roxburghii. The catalyst was prepared through sodium hydroxide and hydrochloric acid treatment of the dried pine leaves; and further functionalized with sulfuric acid treatment to incorporate the acidic functionalities. The synthesized catalyst was characterized by...
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 11 19 شماره
صفحات -
تاریخ انتشار 2009