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Synthesis 2018; 50(07): 1511-1520
DOI: 10.1055/s-0036-1591737
DOI: 10.1055/s-0036-1591737
paper
Intramolecular Cycloaddition Approach to Fused Pyrazoles: Access to 4,5-Dihydro-2H-pyrazolo[4,3-c]quinolines, 2,8-Dihydroindeno[2,1-c]pyrazoles, and 4,5-Dihydro-2H-benzo[e]indazoles
M.J. thanks UGC, New Delhi for a fellowship. Partial Financial support from WB-DBT (GAP 340) is gratefully acknowledged.Further Information
Publication History
Received: 26 September 2017
Accepted after revision: 10 November 2017
Publication Date:
12 December 2017 (online)
Abstract
A straightforward and efficient method for the synthesis of pyrazoles fused with 1,2,3,4-tetrahydroquinoline, 2,3-dihydro-1H-indene, or 1,2,3,4-tetrahydronaphthalene involves the formation of the tosylhydrazone from an aromatic substrate carrying aldehyde and acetylenic functionalities at appropriate positions, followed by base-promoted generation of the diazo compound and subsequent intramolecular 1,3-dipolar cycloaddition. A number of functional groups were found to be compatible for this reaction sequence and yields were moderate to very good (44–95%). A plausible reaction mechanism supported by DFT calculations has been provided to explain the formation of products.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591737. X-ray crystallographic data of 5d, 5e, 6b, and 6d, experimental procedures, and spectral data of compounds 8 and 9 and copies of 1H, 13C NMR spectra of compounds 5–8 and 12 are included.
- Supporting Information
- CIF File
-
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For example:
For a recent review, see:
For structural isomers of dihydroindeno[2,1-c]pyrazoles 6, see:
For structural isomers of 4,5-dihydrobenzo[e]indazoles 7, see:
For structurally related compounds of 7, see: