Novel dehydrative ring transformation of 1-alkyl-3-aroylpyrrolidines into 1-alkyl-2-aryl-3-methylpyrrole derivatives

Mataka, Shuntarō; Kitagawa, Hirohisa; Misumi, Osamu; Tashiro, Masashi; Kamata, Kichinosuke

doi:10.1039/c39930000670

Cited by 3 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Pyrrole 4p , with three different substituents on the pyrrole ring, could be easily constructed by this method (entry 16). It was noted that the methods for the regioselective synthesis of multisubstituted pyrroles with different substituents from the easily accessible starting materials under mild reaction conditions are limited . In addition, azadiene 1j bearing one more substituent (Me group) at the C-2 position could also smoothly react with benzoyl cyanide to give the fully substituted pyrrole 4q in 46% yield (entry 17).…”

Section: Resultsmentioning

confidence: 94%

Reactions of Zirconocene–1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles

Xiong

Xie

et al. 2015

Organometallics

View full text Add to dashboard Cite

Insertion of acyl cyanides into azazirconacyclopentenes derived from 1,3-azadienes has been described, which affords acyl-or non-acyl-substituted pyrroles upon acidic quenching. These reactions are initialized through CO insertion into the azazirconacycle to afford seven-membered oxaazazirconacycles. In the cases of 1,4-or 1,2,4-substituted azadienes, addition of a second molecule of acyl cyanide followed by cyclization upon acidic quenching leads to acyl-substituted pyrroles. In the cases of 1,3,4substituted azadienes, the addition of a second molecule of acyl cyanide cannot proceed due to the steric hindrance caused by the R 3 group on the zirconium intermediate. Acidic quenching of the resulting zirconium intermediate affords non-acyl-substituted pyrroles.

show abstract

Section: Resultsmentioning

confidence: 94%

Reactions of Zirconocene–1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles

Xiong

Xie

et al. 2015

Organometallics

View full text Add to dashboard Cite

show abstract

“…Mataka et al [36] found that the pyrrolidines 59 Ϫ obtainable by easy procedures [37] Ϫ when heated in ethylene glycol for some hours afford 1-alkyl-2-aryl-3-methylpyrroles 60 in high yields. The key step of this ring transformation is the ring opening of the pyrrolidine moiety followed by attack of the nitrogen atom at one of the carbonyl groups as shown in Figure 2.…”

Section: Degenerate Ring Transformations Of Five-membered Heterocymentioning

confidence: 99%

Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives

2001

View full text Add to dashboard Cite

Keywords: Ring opening / Isomerizations / Cyclizations / Heteroaromaticity / RearrangementsRing transformations of five-membered heterocycles and their benzologues for the recent 10 years are discussed and reviewed. These transformations are classified into four groups: (a) ''classical ring transformations'', where the starting and resulting ring system is of the same size, but the heteroatoms and/or their positions have been changed; (b) ''degenerate ring transformations'', where during the course of the transformation the starting compound and product have the same ring system, but the reaction proceeds by a A. IntroductionRearrangements of heterocyclic rings by temporary opening and subsequent closure to a new molecule are of par- [a] (1993). His research interests are mainly devoted to heterocyclic chemistry, synthesis and application of isotopically labelled compounds and, more recently, macrocyclic ring systems with regard to host-guest chemistry.MICROREVIEWS: This feature introduces the readers to the authors' research through a concise overview of the selected topic. Reference to important work from others in the field is included.

show abstract

ChemInform Abstract: Novel Dehydrative Ring Transformations of 1‐Alkyl‐3‐aroylpyrrolidines into 1‐Alkyl‐2‐aryl‐3‐methylpyrrole Derivatives.

et al. 1993

View full text Add to dashboard Cite

show abstract

Novel dehydrative ring transformation of 1-alkyl-3-aroylpyrrolidines into 1-alkyl-2-aryl-3-methylpyrrole derivatives

Abstract: Poly-functionalized pyrroles 4, 5 and 6 were prepared in a good to high yield by a dehydrative ring transformation of 3-aroylpyrrolidine derivatives 1 , 2 and 3 in ethylene glycol a t 130 "C.

Cited by 3 publications

References 1 publication

Reactions of Zirconocene–1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles

Reactions of Zirconocene–1-Aza-1,3-diene Complexes with Acyl Cyanides: Substrate-Dependent Synthesis of Acyl- or Non-Acyl-Substituted Pyrroles

Recent Advances in Ring Transformations of Five-Membered Heterocycles and Their Fused Derivatives

ChemInform Abstract: Novel Dehydrative Ring Transformations of 1‐Alkyl‐3‐aroylpyrrolidines into 1‐Alkyl‐2‐aryl‐3‐methylpyrrole Derivatives.

Contact Info

Product

Resources

About