The formation of 3-ferrocenylpyrazole-4-carboxylates and alkylhydrazine insertion products from α-ferrocenylmethylidene-β-oxocarboxylates

The reactions of α‐ferrocenylmethylidene‐β‐oxocarboxylates (1, 2, 3a, and 3b) with N‐methyl‐ and N‐(2‐hydroxyethyl)hydrazines (5a, 5b) afford ethyl 1‐alkyl‐5‐aryl(methyl)‐3‐ferrocenylpyrazole‐4‐carboxylates (6a, 6b, 6c, 6d, 6e) (∼50%) and N‐alkylhydrazine insertion products, viz., ethyl (N′‐acyl‐N′‐...

Full description

Saved in:
Bibliographic Details
Published in:Journal of heterocyclic chemistry 2011-03, Vol.48 (2), p.441-448
Main Authors: Klimova, Elena I., Klimova, Tatiana, Alamo, Marcos Flores, Stivalet, José M. Méndez, Ramírez, Lena Ruíz, Backinowsky, Leon V., García, Marcos Martínez
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The reactions of α‐ferrocenylmethylidene‐β‐oxocarboxylates (1, 2, 3a, and 3b) with N‐methyl‐ and N‐(2‐hydroxyethyl)hydrazines (5a, 5b) afford ethyl 1‐alkyl‐5‐aryl(methyl)‐3‐ferrocenylpyrazole‐4‐carboxylates (6a, 6b, 6c, 6d, 6e) (∼50%) and N‐alkylhydrazine insertion products, viz., ethyl (N′‐acyl‐N′‐alkylhydrazino)‐3‐ferrocenylpropanoates (7a, 7b, 7c, 7d, 7e) (∼20%) and 1‐acyl‐2‐(N′‐alkyl‐N′‐ethoxycarbonylhydrazino)‐2‐ferrocenylethanes (8a, 8b, 8c, 8d, 8e) (∼10%). The structures of the compounds obtained were established based on the spectroscopic data and X‐ray diffraction analysis (for pyrazoles 6a and 6b). J. Heterocyclic Chem., (2011).
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.613