Chinese Journal of Organic Chemistry >
Synthesis of 12H-Chromeno[2,3-b]quinolin-12-one and 6H-Chromeno[4,3-b]quinolin-6-one from Anthranil
Received date: 2019-03-19
Revised date: 2019-04-19
Online published: 2019-05-06
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.
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.
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]. Chinese Journal of Organic Chemistry, 2019 , 39(9) : 2525 -2533 . DOI: 10.6023/cjoc201903034
[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.
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