Selective N-Alkylation of 2-Amino-4H-chromene-3-carbonitrile Derivatives with Alcohols Catalyzed by AlCl3 Under the Assistance of CH3COOH

doi:10.1007/s40242-019-9248-5

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (6): 997-1001.doi: 10.1007/s40242-019-9248-5

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Selective N-Alkylation of 2-Amino-4H-chromene-3-carbonitrile Derivatives with Alcohols Catalyzed by AlCl₃ Under the Assistance of CH₃COOH

ZHAO Bing¹, HE Yuqian¹, KAN Wei¹, KONG Fengqiao¹, WANG Liyan¹, SONG Bo¹, WANG Wenbo¹, YIN Guangming¹, WANG Jianxin²

1. Chemistry and Chemical Engineering Institute, Qiqihar University, Qiqihar 161006, P. R. China;
2. College of Material Science and Engineering, Qiqihar University, Qiqihar 161006, P. R. China

Received:2019-09-16 Revised:2019-10-28 Online:2019-12-01 Published:2019-11-29
Contact: ZHAO Bing, KAN Wei E-mail:zhao_submit@aliyun.com;kan_submit@aliyun.com
Supported by:
Supported by the National Natural Science Foundation of China(Nos.21506106, 21978410), the Natural Science Foundation of Heilongjiang Province, China(No.LC2017004), the Echelon Reserve Leader Fund for the Leading Talent of Heilongjiang Province, China, the Fundamental Research Project for Universities in Heilongjiang Province, China(Nos.135209209, 135209220, LTSW201735, YSTSXK201853, YSTSXK201859) and the Graduate Innovation Foundation of Qiqihar University, China (No.YJSCX2018-ZD18).

Abstract

Abstract: A highly efficient and selective N-alkylation reaction of 2-amino-4H-chromene-3-carbonitrile derivatives using various alcohols as alkylation agent were developed in the presence of AlCl₃ as a catalyst as well as CH₃COOH as an additive, in which the cyano group kept inert and the amino group was alkylated in high yields. All the target products were characterized and determined by infrared(IR), ¹H NMR, ¹³C NMR, and HRMS. And the X-ray structure of product 3ab was obtained. A bimolecular reaction mechanism catalyzed by AlCl₃ was proposed under the assistance of CH₃COOH.

Key words: N-Alkylation, Alcohol, AlCl₃, CH₃COOH

ZHAO Bing, HE Yuqian, KAN Wei, KONG Fengqiao, WANG Liyan, SONG Bo, WANG Wenbo, YIN Guangming, WANG Jianxin. Selective N-Alkylation of 2-Amino-4H-chromene-3-carbonitrile Derivatives with Alcohols Catalyzed by AlCl₃ Under the Assistance of CH₃COOH[J]. Chemical Research in Chinese Universities, 2019, 35(6): 997-1001.

References

[1] Bradshaw J. S., Krakowiak K. E., Izatt R. M., Tetrahedron, 1992, 4, 4475
[2] Salvatore R. N., Yoon C. H., Jung K. W., Tetrahedron, 2001, 57, 7785
[3] Gawande M. B., Deshpande S. S., Satam J. R., Catal. Commun., 2007, 8, 576
[4] Lee J. Y., Lim K. C., Meng X., Kim S., Synlett., 2010, 11, 1647
[5] Murahashi S. I., Kondo K., Hakata T., Tetrahedron Lett., 1982, 23, 229
[6] Hamid M. H. S. A., Allen C. L., Lamb G. W., Maxwell A. C., Maytum H. C., Watson A. J. A., Williams J. M. J., J. Am. Chem. Soc., 2009, 131, 1766
[7] Gnanaprakasam B., Zhang J., Milstein D., Angew. Chem. Int. Ed., 2010, 122, 1510
[8] Ramachandran R., Prakash G., Selvamurugan S., Viswanathamurthi P., Malecki J. G., Ramkumar V., Dalton. Trans., 2014, 43, 7889
[9] Oldenhuis N. J., Dong V. M., Guan Z., J. Am. Chem. Soc., 2014, 136, 12548
[10] Celaje J. J. A., Zhang X., Zhang F., Kam L., Herron J. R., ACS Catal., 2017, 7, 1136
[11] Yu X. J., He H. Y., Yang L., Fu H. Y., Zheng X. L., Chen H., Catal. Commun., 2017, 95, 54
[12] Liu C. Z., Liao S. H., Li Q., Feng S. L., Sun Q., Yu X., Xu Q., J. Org. Chem., 2011, 76, 5759
[13] Feng S. L., Liu C. Z., Li Q., Yu X. C., Xu Q., Chin. Chem. Lett., 2011, 22, 1021
[14] Kwon M. S., Kim S., Park S., Bosco W., Chidrala R. K., Park J., J. Org. Chem., 2009, 74, 2877
[15] Zhang Y., Qi X. J., Cui X. J., Shi F., Deng Y. Q., Tetrahedron Lett., 2011, 52, 1334
[16] Jiang L., Jin L. L., Tian H. W., Yuan X. Q., Yu X. C., Q. Xu, Chem. Commun., 2011, 47, 10833
[17] Dang T. T., Ramalingam B., Shan S. P., Seayad A. M., ACS Catal., 2013, 3, 2536
[18] Mohanty A., Roy S., Tetrahedron Lett., 2016, 57, 2749
[19] Shi F., Tse M. K., Zhou S. L., Pohl M. M., Radnik J., Hübner S., Jähnisch K., Brückner A., Beller M., J. Am. Chem. Soc., 2009, 131, 1775
[20] Nayal O. S., Thakur M. S., Kumar M., Kumar N., Maurya S. K., Adv. Synth. Catal., 2018, 360, 730
[21] Cui X. J., Shi F., Zhang Y., Deng Y. Q., Tetrahedron Lett., 2010, 51, 2048
[22] Trillo P., Baeza A., Nájera C., Eur. J. Org. Chem., 2012, 2929
[23] Zhang E. L., Tian H. W., Xu S. D., Yu X. C., Xu Q., Org. Lett., 2013, 15, 2704
[24] Sun J., Jin X. D., Zhang F. W., Hu W. Q., Liu J. T., Li R., Catal. Commun., 2012, 24, 30
[25] Shimizu K., Imaiida N., Kon K., Siddiki S. M. A. H., Satsuma A., ACS Catal., 2013, 3, 998
[26] Shimizu K., Kanno S., Kon K., Siddiki S. M. A. H., Tanaka H., Sakata Y., Catal. Today, 2014, 232, 134
[27] Das J., Banerjee D., J. Org. Chem., 2018, 83, 3378
[28] Jimenez M. V., Fernandez-Tornos J., Gonzalez-Lainez M., Sanchez-Page B., Modrego F. J., Oro L. A., Perez-Torrente J. J., Catal. Sci. Technol., 2018, 8, 2381
[29] Kerdphon S., Quan X., Parihar V. S., Andersson P. G., J. Org. Chem., 2015, 80, 11529
[30] Ghosh S. C., Ngiam J. S. Y., Seayad A. M., Tuan D. T. C., Chai L. L., Chen A. Q., J. Org. Chem., 2012, 77, 8007
[31] Shan S. P., Xiaoke X., Gnanaprakasam B., Dang T. T., Ramalingam B., Huynh H. V., Seayad A. M., RSC Adv., 2015, 5, 4434
[32] Whittaker A. M., Dong V. M., Angew. Chem. Int. Ed., 2015, 54, 1312
[33] Liu H., Wang D. L., Chen X., Lu Y., Zhao X. L., Liu Y., Green Chem., 2015, 19, 1109
[34] Bala M., Verma P. K., Sharma U., Kumar N., Singh B., Green Chem., 2013, 15, 1687
[35] Wang N. N., Zou X. Y., Ma J., Li F., Chem. Commun., 2014, 50, 8303
[36] Jiang X., Tang W. J., Xue D., Xiao J. L., Wang C., ACS Catal., 2017, 7, 1831
[37] Gunanathan C., Ben-David Y., Milstein D., Science, 2007, 317, 790
[38] Fujita K., Komatsubara A., Yamaguchi R., Tetrahedron, 2009, 65, 3624
[39] Xu Q., Li Q., Zhu X. G., Chen J. H., Adv. Synth. Catal., 2013, 355, 73
[40] Sandhya K. S., Suresh C. H., Organometallics, 2013, 32, 2926
[41] Dev K., Ramakrishna E., Maurya S. W., Siddiqui I. R., Kant R., Maurya R., Tetrahedron Lett., 2017, 58, 1202
[42] Anbarasu G., Malathy M., Karthikeyan P., Rajavel R., J. Solid. State. Chem., 2017, 253, 305
[43] Cui X. J., Zhang Y., Shi F., Deng Y. Q., Chem-Eur J., 2011, 17, 1021
[44] Anxionnat B., Pardo D. G., Ricci G., Cossy J., Eur. J. Org. Chem., 2012, 4453
[45] Wang G. W., Shen Y. B., Wu X. L., Eur. J. Org. Chem., 2008, 4367
[46] Li F., Shan H. X., Kang Q. K., Chen L., Chem. Commun., 2011, 47, 5058
[47] Fan X. H., Fu L. A., Li N., Lv H., Cui X. M., Qi Y., Org. Biomol. Chem., 2013, 11, 2147
[48] Xu Q., Xie H. M., Zhang E. L., Ma X. T., Chen J. H., Yu X. C., Li H., Green Chem., 2016, 18, 3940
[49] Aswin K., Mansoor S. S., Logaiya K., Sudhan S. P. N., Malik V. S., Ramadoss H., Res. Chem. Intermed., 2014, 40, 2583
[50] Li Y. Q., Chen Y. B., Huang Z. Z., Chin. Chem. Lett., 2014, 25, 1540

Selective N-Alkylation of 2-Amino-4H-chromene-3-carbonitrile Derivatives with Alcohols Catalyzed by AlCl₃ Under the Assistance of CH₃COOH

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