Synthesis of polysubstituted pyrroles from sulfinimines (N-sulfinyl imines)
نویسندگان
چکیده
منابع مشابه
A straightforward one-pot multicomponent synthesis of polysubstituted pyrroles.
Polysubstituted pyrroles were efficiently synthesized in moderate yields by a one-pot multicomponent reaction starting from primary amines, ethyl glyoxalate and 2-bromoacetophenones in the presence of pyridine in refluxing acetonitrile. This methodology was utilized to synthesize a highly substituted benz[g]indole.
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Carbamoyl anions, generated from N,N-disubstituted formamides and lithium diisopropylamide, add with high diastereoselectivity to chiral N-sulfinyl aldimines and ketimines to provide α-amino amides. The methodology enables the direct introduction of a carbonyl group without the requirement of unmasking steps as with other nucleophiles. The products may be converted to α-amino esters or 1,2-diam...
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We have developed an organocatalyzed three-component reaction of 1,2-diones, aldehydes and arylamines, which provides an efficient approach to access polysubstituted pyrroles. In the catalysis of 4-methylbenzenesulfonic acid monohydrate, the reactions of a wide range of 1,2-diones, arylamines and aldehydes took place smoothly to generate the corresponding polysubstituted pyrroles in acceptable ...
متن کاملSynthesis of polysubstituted pyrroles via [3 + 2]-annulation of aziridines and β-nitroalkenes under aerobic conditions.
Polysubstituted pyrroles were regioselectively synthesized in moderate to good yields via the copper acetate-catalyzed [3 + 2] annulation reaction of readily accessible aziridines and nitroalkenes. This reaction was proposed to proceed through a key azomethine ylide intermediate generated by selective C-C bond cleavage of the aziridine followed by annulation with nitroalkenes under aerobic cond...
متن کاملAn Efficient Procedure for the Synthesis of Polysubstituted Pyrroles in an Ionic Liquid
The ionic liquid 1-butyl-3-methyl-imidazolium hydrogen sulfate, [bmim]HSO4, was used as a catalyst and reaction medium for the pyrrole synthesis, and a wide range of aliphatic, aromatic, heteroaromatic and carboxylic 1,4-diketones easily underwent condensations with aniline and ethylenediamine to form polysubstituted pyrroles. Sequential decarboxylation/Paal-Knorr pyrrole condensation was obser...
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ژورنال
عنوان ژورنال: Tetrahedron
سال: 2008
ISSN: 0040-4020
DOI: 10.1016/j.tet.2008.02.102