Synthesis of 2H-pyrrolo[3,4-C]quinoline via an Aldol/Van Leusen/Staudinger/aza-Wittig sequence |
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| Authors: | Yu-Qing Shi Li-De Liao Yang-Gen Hu Hua Cheng Song Wang |
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| Institution: | 1. College of Chemical Engineering and Food Science, Xiangyang, China;2. Hubei Key Laboratory of Wudang Local Chinese Medicine Research and Department of Pharmacy of Taihe Hospital, Hubei University of Medicine, Shiyan, China;3. Hubei Key Laboratory of Low Dimensional Optoelectronic Materials and Device, Hubei University of Arts and Science, Xiangyang, China |
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| Abstract: | An aldol/van Leusen/Staudinger/aza-Wittig reaction for the preparation of the derivatives of 2H-pyrrolo3,4-c]quinolines from 2-azidobenzaldehyde, acetyl compounds, and tosylmethyl isocyanide was developed. The process involves an aldol condensation of 2-azidobenzaldehyde with acetyl compound in base, a van Leusen reaction to form the key pyrrole intermediates, and then a Staudinger and intramolecular aza-Wittig reaction occurred with the addition of triphenylphosphine to complete the formation of pyrrolo3,4-c]quinoline ring in high yields. |
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| Keywords: | Aldol/van Leusen/Staudinger/aza-Wittig reaction 2-azidobenzaldehyde 2H-pyrrolo[3 4-c]quinolones pyrrole |
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