Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

LiOtBu-Promoted Intramolecular Cycloaddition of 2’-Alkynyl-Biaryl-2-Aldehyde N-Tosylhydrazones Approach to 3-Substituted 1H-Dibenzo[e,g]indazoles

Version 1 : Received: 10 October 2023 / Approved: 10 October 2023 / Online: 11 October 2023 (03:59:02 CEST)

A peer-reviewed article of this Preprint also exists.

Lv, J.; Hua, R. LiOtBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde N-Tosylhydrazones Approach to 3-Substituted 1H-Dibenzo[e,g]indazoles. Molecules 2023, 28, 8061. Lv, J.; Hua, R. LiOtBu-Promoted Intramolecular 1,3-Dipolar Cycloaddition of the 2′-Alkynyl-biaryl-2-aldehyde N-Tosylhydrazones Approach to 3-Substituted 1H-Dibenzo[e,g]indazoles. Molecules 2023, 28, 8061.

Abstract

A two-step, one-pot synthesis of 3-substituted 1H-dibenzo[e,g]indazoles in good to high yields via a LiOtBu-promoted intramolecular cyclization of 2’-alkynyl-biaryl-2-aldehyde N-tosylhydrazones, formed in situ by the reactions of 2’-alkynyl-biaryl-2-aldehydes with p-methylbenzenesulfonohydrazide was developed. Two kinds of hydrogen bonds forming in several products were observed in DMSO-d6 solution in 1H NMR spectroscopic data, which were assigned to the formation of solvated products and dimers of products, supported by the studies of density functional theory (DFT).

Keywords

N-tosylhydrazones; 1H-dibenzo[e,g]indazoles; intramolecular cycloaddition; lithium tert-butoxide; hydrogen bonds

Subject

Chemistry and Materials Science, Organic Chemistry

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