Transition-metal-free synthesis of polysubstituted pyrrole derivatives via cyclization of methyl isocyanoacetate with aurone analogues

Presented herein is an unprecedented transition-metal-free cyclization of methyl isocyanoacetate with aurone analogues catalyzed by NaOH. Various 2,3,4-trisubstituted pyrroles were obtained in excellent yields (up to 99%). The high efficiency of this synthetic procedure, coupled with the operational...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 16; no. 30; pp. 5422 - 5426
Main Authors Wang, Zhi-Peng, He, Yun, Shao, Pan-Lin
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 2018
Royal Society of Chemistry
Subjects
Atom economy
Chemistry
Chemistry, Organic
Physical Sciences
Pyrroles
Science & Technology
Sodium hydroxide
Synthesis
ASSISTED SYNTHESIS
ASYMMETRIC-SYNTHESIS
ENANTIOSELECTIVE SYNTHESIS
OLIGOSUBSTITUTED PYRROLES
ACID-CHLORIDES
1,3-DIPOLAR CYCLOADDITION
ISOCYANIDES
REGIOSELECTIVE SYNTHESIS
CATALYZED REACTION
TETRASUBSTITUTED PYRROLES
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Summary:Presented herein is an unprecedented transition-metal-free cyclization of methyl isocyanoacetate with aurone analogues catalyzed by NaOH. Various 2,3,4-trisubstituted pyrroles were obtained in excellent yields (up to 99%). The high efficiency of this synthetic procedure, coupled with the operational simplicity and atom economy, makes it an attractive method for the synthesis of polysubstituted pyrroles.
Bibliography:ObjectType-Article-1
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/C8OB01558A