Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil

doi:10.6023/cjoc201903034

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2525-2533.DOI: 10.6023/cjoc201903034 Previous Articles Next Articles

ARTICLE

由氨茴内酐合成12H-色烯[2,3-b]喹啉-12-酮和6H-色烯[4,3-b]喹啉-6-酮

孙婉婉, 毛玉健, 蒋静, 余靓, 陈凌云, 胡延维, 张士磊

江苏省重大神经精神疾病研究重点实验室苏州大学药学院苏州 215123

收稿日期:2019-03-19 修回日期:2019-04-19 发布日期:2019-05-06
通讯作者: 胡延维, 张士磊 E-mail:huyanwei@suda.edu.cn;zhangshilei@suda.edu.cn
基金资助:
国家自然科学基金（No.21202112）、教育部博士点基金新教师类项目（No.20123201120019）、江苏高校优势学科建设工程资助项目.

Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil

Sun Wanwan, Mao Yujian, Jiang Jing, Yu Jing, Chen Lingyun, Hu Yanwei, Zhang Shilei

Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, Suzhou 215123

Received:2019-03-19 Revised:2019-04-19 Published:2019-05-06
Contact: 10.6023/cjoc201903034 E-mail:huyanwei@suda.edu.cn;zhangshilei@suda.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202112), the Ph.D. Programs Foundation of Ministry of Education (No. 20123201120019) and the Priority Academic Program Development of Jiangsu Higher Education Institutions.

1. Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil.PDF(2967KB)

Abstract

Two heterocyclic compounds 12H-chromeno[2,3-b]quinolin-12-one and 6H-chromeno[4,3-b]quinolin-6-one could be synthesized by the reaction of anthranil with 4-hydroxycoumarin under high temperature conditions. The reaction is a thermo-promoted transformation, without the assistance of catalysts or additives, and without the generation of toxic wastes. This one-step reaction is superior to other reported methods for the preparation of such heterocycles.

Key words: high-temperature reaction, anthranil, 4-hydroxycoumarin, synthesis of heterocycles

Cite this article

Sun Wanwan, Mao Yujian, Jiang Jing, Yu Jing, Chen Lingyun, Hu Yanwei, Zhang Shilei. Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil[J]. Chin. J. Org. Chem., 2019, 39(9): 2525-2533.

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[1] Jin, H.-M.; Huang, L.; Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2016, 55, 794.
[2] Jin, H.-M.; Tian, B.; Song, X.-L.; Xie, J.; Rudolph, M.; Rominger, F.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2016, 55, 12688.
[3] Li, L.; Wang, H.; Yu, S.-J.; Yang, X.-F.; Li, X.-W. Org. Lett. 2016, 18, 3662.
[4] Yu, S.-J.; Tang, G.-D.; Li, Y.-Z.; Zhou, X.-K.; Lan, Y.; Li, X.-W. Angew. Chem. Int. Ed. 2016, 55, 8696.
[5] Yu, S.-J.; Li, Y.-Y.; Zhou, X.-K.; Wang, H.; Kong, L.-H.; Li, X.-W. Org. Lett. 2016, 18, 2812.
[6] Wang, M.-M.; Kong, L.-H.; Wang, F.; Li, X.-W. Adv. Synth. Catal. 2017, 359, 4411.
[7] Zou, M.-C.; Liu, J.-Z.; Tang, C.-H.; Jiao, N. Org. Lett. 2016, 18, 3030.
[8] Shi, L.-L.; Wang, B.-Q. Org. Lett. 2016, 18, 2820.
[9] Biswas, A.; Karmakar, U.; Nandi, S.; Samanta, R. J. Org. Chem. 2017, 82, 8933.
[10] Wang, F.; Xu, P.; Wang, S.-Y.; Ji, S.-J. Org. Lett. 2018, 20, 2204.
[11] Wang, Z.-H.; Zhang, H.-H.; Wang, D.-M.; Xu, P.-F.; Luo, Y.-C. Chem. Comm. 2017, 53, 8521.
[12] Sahani, R. L.; Liu, R. S. Angew. Chem. Int. Ed. 2017, 56, 12736.
[13] Lei, X.-Q.; Gao, M.-H.; Tang, Y.-F. Org. Lett. 2016, 18, 4990.
[14] Tiwari, D. K.; Phanindrudu, M.; Wakade, S. B.; Nanubolu, J. B.; Tiwari, D. K. Chem. Commun. 2017, 53, 5302.
[15] Wakade, S. B.; Tiwari, D. K.; Ganesh, P. S. K. P.; Phanindrudu, M.; Likhar, P. R.; Tiwari, D. K. Org. Lett. 2017, 19, 4948.
[16] Jiang, J.; Cai, X.; Hu, Y.-W.; Liu, X.-J.; Chen, X.-D.; Wang, S.-Y.; Zhang, Y.-N.; Zhang, S.-L. J. Org. Chem. 2019, 84, 2022.
[17] Qian, P.-F.; Wan, H.-X.; Jiang, J.; Hu, Y.-W.; Chen, X.-B.; Zhang, S.-L. Chin. J. Org. Chem. 2016, 36, 1878.
[18] Weng, Y.-Y.; Zhou, H.; Sun, C.; Xie, Y.-Y.; Su, W.-K. J. Org. Chem. 2017, 82, 9047.
[19] Thigulla, Y.; Kumar, T. U.; Trivedi, P.; Ghosh, B.; Bhattacharya, A. ChemistrySelect 2017, 2, 2721.
[20] Sashidhara, K. V.; Palnati, G. R.; Singh, L. R.; Upadhyay, A.; Avula, S. R.; Kumara, A.; Kant, R. Green Chem. 2015, 17, 3766.
[21] Rajawinslin, R. R.; Gawande, S. D.; Kavala, V.; Huang, Y.-H.; Kuo, C.-W.; Kuo, T.-S.; Chen, M.-L.; He, C.-H.; Yao, C.-F. RSC Adv. 2014, 4, 37806.
[22] Wu, J.; Wang, X.-C. Org. Biomol. Chem. 2006, 4, 1348.
[23] Ishigu, T.; Ukawa, K.; Sugihara, H.; Nohara, A. Heterocycles 1981, 16, 733.
[24] Hansch, C.; Sammes, P.; Taylor, J. Comprehensive Medicinal Chemistry, Pergamon, London, 1990, Vol. 6.
[25] Singh. G.; Singh, R.; Girdhar, N. K.; Ishar, M. P. S. Tetrahedron 2002, 58, 2471.
[26] Marsais, F.; Godard, A.; Queguiner, G. J. Heterocycl. Chem. 1989, 26, 1589.
[27] Zhang, X.-Y.; Guo, X.-J.; Fang, L.-L.; Song, Y.-P.; Fan, X.-S. Eur. J. Org. Chem. 2013, 8087.
[28] Singh, J. B.; Mishra, K.; Gupta, T.; Singh, R. M. ChemistrySelect 2017, 2, 1207.
[29] Weng, Y.-Y.; Zhou, H.; Sun, C.; Xie, Y.-Y.; Su, W.-K. J. Org. Chem. 2017, 82, 9047.

由氨茴内酐合成12H-色烯[2,3-b]喹啉-12-酮和6H-色烯[4,3-b]喹啉-6-酮

Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil

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