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

Moumita Jash; Bimolendu Das; Suparna Sen; Chinmay Chowdhury

doi:10.1055/s-0036-1591737

Synthesis, Inhaltsverzeichnis

Synthesis 2018; 50(07): 1511-1520
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

Moumita Jash

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in

,

Bimolendu Das

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in

,

Suparna Sen

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in

,

Chinmay Chowdhury*

Organic & Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology, 4, Raja S. C. Mullick Road, Kolkata-700032, India eMail: chinmay@iicb.res.in

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Abstract

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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.

Key words

cycloaddition - pyrazole - indazole - dihydroquinoline - quinoline

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Referenzen

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