Silver Nitrate Mediated Cyclization/N–N Bond-Cleavage Reaction for the Synthesis of 3-Arylisoquinolines

Yun-Hui Zhao; Yubo Li; Mingjian Luo; Zilong Tang; Keqin Deng

doi:10.1055/s-0035-1562609

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(18): 2597-2600
DOI: 10.1055/s-0035-1562609

letter

Silver Nitrate Mediated Cyclization/N–N Bond-Cleavage Reaction for the Synthesis of 3-Arylisoquinolines

Autor*innen

Yun-Hui Zhao*

^aHunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, P. R. of China eMail: zhao_yunhui@163.com

^bKey Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
Yubo Li

^aHunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, P. R. of China eMail: zhao_yunhui@163.com
Mingjian Luo

^aHunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, P. R. of China eMail: zhao_yunhui@163.com
Zilong Tang

^cKey Laboratory of Theoretical Chemistry and Molecular Simulation, Ministry of Education, Xiangtan, Hunan, 411201, P. R. of China
Keqin Deng

^aHunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201, P. R. of China eMail: zhao_yunhui@163.com

^cKey Laboratory of Theoretical Chemistry and Molecular Simulation, Ministry of Education, Xiangtan, Hunan, 411201, P. R. of China

Abstract

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Abstract

An unprecedented silver nitrate mediated novel transformation of aromatic hydrazones into various isoquinolines has been developed. This method involves a silver nitrate promoted cyclization of aromatic hydrazones followed by N–N bond cleavage, and has wide substrate scope under mild conditions.

Key words

isoquinolines - bond cleavage - hydrazones - silver nitrate - alkynals - domino reactions

Volltext

Referenzen

References and Notes

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12 3-Phenylisoquinolines (2a); ¹³ Typical ProcedureTo a solution of 2-(phenylethynyl)benzaldehyde (1a; 62.0 mg, 0.3 mmol) in EtOH (5 mL) was added N₂H₄·HCl (30.6 mg, 0.45 mmol), and the mixture was stirred at r.t. for 3 h. The solid was then collected by filtration and used in the next step without further purification. The crude aromatic hydrazones 3a was dissolved in DMSO (3 mL) and AgNO₃ (51.0 mg, 0.3 mmol) was added. The mixture was stirred at 100 °C until all starting material was consumed. The solvent was evaporated and the residue was purified by column chromatography, eluting with hexanes/EtOAc (5:1) to give a white solid; yield: 35 mg (57%); mp 97–99 °C; ¹H NMR (500 MHz, CDCl₃): δ = 9.37 (s, 1 H), 8.16 (d, J = 7.5 Hz, 2 H), 8.10 (s, 1 H), 8.02 (d, J = 8.0 Hz, 1 H), 7.91–7.89 (d, J = 8.0 Hz, 1 H), 7.75–7.70 (m, 1 H), 7.63–7.60 (m, 1 H), 7.56–7.53 (m, 2 H), 7.47–7.44 (m, 1 H); ¹³C NMR (125 MHz, CDCl₃): δ = 152.5 , 151.3, 139.6, 136.7, 130.6, 128.8, 128.6, 127.8, 127.6, 127.1, 127.0, 126.9, 116.6. The NMR data agreed with those previously reported.
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Zusatzmaterial

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