Synthesis of N,N-Isoquinoline Dipoles via Intramolecular Cyclization of o-Alkynylbenzaldehyde Hydrazones

doi:10.11944/j.issn.1000-0518.2017.07.160456

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (7): 795-800.DOI: 10.11944/j.issn.1000-0518.2017.07.160456

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Synthesis of N,N-Isoquinoline Dipoles via Intramolecular Cyclization of o-Alkynylbenzaldehyde Hydrazones

SHI Yun(),LI Mengsheng,WEI Xiaolin

College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,China

Received:2016-11-11 Accepted:2017-02-23 Published:2017-07-04 Online:2017-07-04
Contact: SHI Yun
Supported by:
Supported by Gansu Province Youth Science and Technology Fund Project(No.1107RJYA080)

Abstract

Abstract:

N,N-Isoquinoline dipole derivatives were synthesized via intramolecular cyclization of o-alkynylbenzaldehyde hydrazones in the presence of silver acetate(AgOAc) in dichloromethane(DCM) at room temperature. The chemical structures of these obtained products were characterized by mass spectrometry and nuclear magnetic resonance spectroscopy(NMR). In addition, the effect of catalysts and their loadings, raw material ratios, solvents and temperatures on the yields was investigated. The target compound (3-(((methoxycarbonyl)oxy)methyl)isoquinolin-2-iu-m-2-yl)(tosyl)-amide is obtained in 60% yield and the substrate adaptability can be up to 85% under optimum conditions. This method has advantages of easy operation, mild reaction condition and functional group tolerance. Through the exploration of experimental conditions and substrate applicability, this paper solves the disadvantages and shortcomings of the method of synthesizing isoquinoline dipole compounds in the past, which provides a new experimental method for the preparation of compounds containing such skeletons.

Key words: o-alkynylbenzaldehyde hydrazone, silver-catalyzed, N, N-isoquinoline dipole

SHI Yun, LI Mengsheng, WEI Xiaolin. Synthesis of N,N-Isoquinoline Dipoles via Intramolecular Cyclization of o-Alkynylbenzaldehyde Hydrazones[J]. Chinese Journal of Applied Chemistry, 2017, 34(7): 795-800.

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Synthesis of N,N-Isoquinoline Dipoles via Intramolecular Cyclization of o-Alkynylbenzaldehyde Hydrazones

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