Phosphoric Acid-Catalyzed Double/Triple Pictet-Spengler Annulation/Oxidative Aromatization for Construction of C2- and C3-Symmetrical Quinazolinones

doi:10.6023/cjoc202508003

Chinese Journal of Organic Chemistry ›› 2026, Vol. 46 ›› Issue (3): 1070-1077.DOI: 10.6023/cjoc202508003 Previous Articles Next Articles

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膦酸催化的双/三次Pictet-Spengler缩合/氧化芳构化构建C₂和C₃对称的喹啉酮

黄泽宁, 左凯丞, 胡涛, 张澄阳, 张金龙^*(), 蒋高喜^*()

苏州科技大学材料科学与工程学院江苏苏州 215009

收稿日期:2025-10-14 修回日期:2025-10-29 发布日期:2025-11-19
通讯作者: 张金龙, 蒋高喜
基金资助:
苏州科技大学资助项目

Phosphoric Acid-Catalyzed Double/Triple Pictet-Spengler Annulation/Oxidative Aromatization for Construction of C₂- and C₃-Symmetrical Quinazolinones

Zening Huang, Kaicheng Zuo, Tao Hu, Chengyang Zhang, Jinlong Zhang^*(), Gaoxi Jiang^*()

School of Materials Science and Engineering, Suzhou University of Science and Technology, Suzhou, Jiangsu 215009

Received:2025-10-14 Revised:2025-10-29 Published:2025-11-19
Contact: Jinlong Zhang, Gaoxi Jiang
Supported by:
Suzhou University of Science and Technology

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Abstract

A practical phosphoric acid-catalysed double/triple Pictet-Spengler annulation/oxidative aromatization has been developed to synthesize a series of C₂- and C₃-symmetrical quinazolinones from 2-aminobenzamides and aldehydes. The products can be easily transformed into various valuable aromatic diamines and triamines with different substitute side chains in gram-scale, which might be potential for exploration of new functional materials.

Key words: phosphoric acid-catalysis, Pictet-Spengler annulation, C₂/C₃-symmetry, quinazolinone

Cite this article

Zening Huang, Kaicheng Zuo, Tao Hu, Chengyang Zhang, Jinlong Zhang, Gaoxi Jiang. Phosphoric Acid-Catalyzed Double/Triple Pictet-Spengler Annulation/Oxidative Aromatization for Construction of C₂- and C₃-Symmetrical Quinazolinones[J]. Chinese Journal of Organic Chemistry, 2026, 46(3): 1070-1077.

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Fig. & Tab. 5

Scheme 1. Design and synthesis of C2- and C3-symmetrical quinazolinones and diamines/triamines

Table 1. Scopes of both 2-aminobenzamides 1 and aldehydes 2 for the synthesis of a series of C2- and C3-symmetrical quinazolinonesa

Scheme 2. Reaction of 1a with the cyclohexane-1,4-dione 2h

Scheme 3. Reasonable reaction mechanism

Table 2. Synthesis of C2- and C3-symmetrical aromatic amines and aldehyde

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膦酸催化的双/三次Pictet-Spengler缩合/氧化芳构化构建C₂和C₃对称的喹啉酮

Phosphoric Acid-Catalyzed Double/Triple Pictet-Spengler Annulation/Oxidative Aromatization for Construction of C₂- and C₃-Symmetrical Quinazolinones

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