Regioselective Synthesis of Mono‐ and Dispiropyrazoline Derivatives via 1,3‐dipolar Cycloaddition with Nitrilimines

The 1,3‐dipolar cycloaddition reaction of (E,E)‐1,3‐bis(arylidene)indan‐2‐one 1a, 1b, 1c, 1d, 1e with diarylnitrilimines, generated in situ via dehydrohalogenation of the corresponding hydrazonoyl chlorides 2a, 2b, 2c, affords predominantly monospiropyrazolines 3 and 4 as a mixture of diastereoisome...

Full description

Saved in:
Bibliographic Details
Published in:Journal of heterocyclic chemistry 2017-03, Vol.54 (2), p.1152-1160
Main Authors: Rouatbi, Fadwa, Mhiri, Chourouk, Askri, Moheddine, Knorr, Michael, Rousselin, Yoann, Kubicki, Marek M.
Format: Article
Language:English
Subjects:
Chemical Sciences
Crystals
Diffraction
X-rays
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 1,3‐dipolar cycloaddition reaction of (E,E)‐1,3‐bis(arylidene)indan‐2‐one 1a, 1b, 1c, 1d, 1e with diarylnitrilimines, generated in situ via dehydrohalogenation of the corresponding hydrazonoyl chlorides 2a, 2b, 2c, affords predominantly monospiropyrazolines 3 and 4 as a mixture of diastereoisomers. Also dispiropyrazolines 5 are formed in moderate yields. The structure and stereochemistry of cycloadducts 3, 4, 5 were confirmed by 1H and 13C‐NMR spectroscopy, elemental analyses data, and single‐crystal X‐ray diffraction studies of 3ba and 5ca.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2684