2017
DOI: 10.1039/c7ra11216e
|View full text |Cite
|
Sign up to set email alerts
|

Tandem intramolecular cyclisation/1,3-aryl shift in N-(4,4-diethoxybutyl)-1-arylmethanimines (Kazan reaction): synthesis of 3-benzylidene-1-pyrrolines

Abstract: A novel tandem reaction, which transforms N-(4,4-diethoxybutyl)imines to 3-arylidene-1-pyrrolines via intramolecular Mannich reaction/[1,3]-sigmatropic rearrangement of the aryl fragment is described.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
3
1
1

Citation Types

2
7
0

Year Published

2019
2019
2024
2024

Publication Types

Select...
7

Relationship

2
5

Authors

Journals

citations
Cited by 18 publications
(9 citation statements)
references
References 34 publications
2
7
0
Order By: Relevance
“…The importance of nucleophilicity‐basicity balance of nitrogen atom in reactions under consideration is demonstrated by behavior of N ‐(4,4‐diethoxybutyl)arylimines 22 in the presence of acids . An interaction of these compounds with various phenols leads to mixtures of unidentified products, whereas in the absence of aromatic nucleophiles they easily undergo intramolecular cyclization to pyrrolidine derivatives 23 .…”
Section: Introductionmentioning
confidence: 99%
“…The importance of nucleophilicity‐basicity balance of nitrogen atom in reactions under consideration is demonstrated by behavior of N ‐(4,4‐diethoxybutyl)arylimines 22 in the presence of acids . An interaction of these compounds with various phenols leads to mixtures of unidentified products, whereas in the absence of aromatic nucleophiles they easily undergo intramolecular cyclization to pyrrolidine derivatives 23 .…”
Section: Introductionmentioning
confidence: 99%
“…We started our work from the study of the reaction of commercially available 3-methyl-1-( p -tolyl)-1 H -pyrazol-5-amine 2a with iminium salt 1a , which is easily accessible according to the known procedure (see Table ). We first performed the reaction at room temperature in chloroform; however, this did not provide the expected result (Table , entry 1).…”
Section: Resultsmentioning
confidence: 99%
“…These data and our deep interest in the chemistry of 1-pyrrolines , led us to investigate the behavior of N -nucleophiles in this reaction. As a result of our research, herein, we report the synthesis of pyrazolo­[3,4- b ]­pyridines via the reaction of 3-arylidene-1-pyrrolines with aminopyrazole derivatives.…”
Section: Introductionmentioning
confidence: 99%
“…Transformation of the benzo[c]benzo [6,7]indeno[2,1-c]fluorene scaffold in Precursor to phenanthro(2.1,10,9,8,7-pqrstuv)pentaphene in Moth would formally require an unusual 1,3aryl shift. [45] Another mechanism could be rearrangement by radicalinduced processes similar to those proposed by Kartney et al for the rearrangement of triphenylenes. [46] Following this line of thought, the first step would involve the cleavage of an Csp 2 -Csp 3 bond of the dibenzocyclopentadiene ring resulting in the formation of a biradical.…”
Section: Introductionmentioning
confidence: 81%