Synthesis of novel polysubstituted N-benzyl-1H-pyrroles via a cascade reaction of alkynyl Fischer carbenes with alpha-imino glycine methyl esters

An efficient and simple synthesis of novel and densely substituted N-benzyl-1H-pyrroles 6a-r is described by a 1,4-addition/isomerization/ring closure/demetalation cascade process of alkynyl Fischer carbene complexes 1a-f and 2a and a-imino glycine methyl esters 3a, b, d, g, h, and k promoted with L...

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Published inOrganic & biomolecular chemistry Vol. 13; no. 48; pp. 11753 - 11760
Main Authors de la Cruz, Fabiola N., Lopez, Julio, Jimenez-Halla, J. Oscar C., Flores-Alamo, Marcos, Tamariz, Joaquin, Delgado, Francisco, Vazquez, Miguel A.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 28.12.2015
Subjects
Chemistry
Chemistry, Organic
Glycine - analogs & derivatives
Glycine - chemistry
Imines - chemistry
Methane - analogs & derivatives
Methane - chemistry
Molecular Structure
Physical Sciences
Pyrroles - chemical synthesis
Science & Technology
1,3-DIPOLAR CYCLOADDITIONS
TRANSITION-METAL-COMPLEXES
DIELS-ALDER REACTIONS
(1-ALKYNYL)CARBENE COMPLEXES
PHOTOCHEMICAL-REACTION
SUBSTITUTED PYRROLES
ORGANIC SYNTHESES
HIGHLY EFFICIENT SYNTHESIS
INTERMOLECULAR RADICAL REACTIONS
MICHAEL ADDITION
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Summary:An efficient and simple synthesis of novel and densely substituted N-benzyl-1H-pyrroles 6a-r is described by a 1,4-addition/isomerization/ring closure/demetalation cascade process of alkynyl Fischer carbene complexes 1a-f and 2a and a-imino glycine methyl esters 3a, b, d, g, h, and k promoted with LDA.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01655j