Studies on the New Method for Syntheses of 1H-Indazoles (Ⅰ)

Chem. J. Chinese Universities ›› 1993, Vol. 14 ›› Issue (8): 1096.

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Studies on the New Method for Syntheses of 1H-Indazoles (Ⅰ)

ZHONG Zhen-Qi¹, XU Tong-Sheng¹, CHEN Xiao-Nai², QIU Yu-Zhu³, HU Hong-Wen³

1. Department of Organic Chemistry, Henan Medical University, Zhengzhou, 450052;
2. Tumor Institute of Henan Medical University;
3. Department of Chemistrty, Nanjing University

Received:1992-11-30 Revised:1993-05-10 Online:1993-08-24 Published:1993-08-24

Abstract

Abstract: In this paper, we put forward a new and convenient method for the synthesis of 1H-indazoles.In the presence of PPA, the cyclization of a series of 2,6-dialkoxyl (or hydroxy)ace-tophenone hydrazones(2_{_a-f}) gave 3-methyl-4-alkoxyl (or hydroxy)-1H-indazoles (3_a-f).This new method offers several advantages: easy access of the reagents, reasonable yield and short reaction time.We also studied its applied range.The application of this method to 2-methoxy-4,6-dimethylacetophenone hydrazone (2_g) gave 3, 4,6-trimethyl^-1H-indazole (3_g).But the application of it to salicyaldehyde, o-methoxybenzaldehyde, 2,4-dihydroxybenzaldehyde or o-hydroxy-acetophenone, 2-hydroxy-3, 5-dimethylacetophenone hydrazones (2_h-l) could not bring about ring closure, resulted in the formation of the corresponding azines (3_h-l) in excellent yields.

Key words: Hydrazone, PPA, Indazole, Azine

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ZHONG Zhen-Qi, XU Tong-Sheng, CHEN Xiao-Nai, QIU Yu-Zhu, HU Hong-Wen. Studies on the New Method for Syntheses of 1H-Indazoles (Ⅰ)[J]. Chem. J. Chinese Universities, 1993, 14(8): 1096.

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Studies on the New Method for Syntheses of 1H-Indazoles (Ⅰ)

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