Chinese Journal of Organic Chemistry >
One-Pot Reductive Amination/N-Acylation/Aza-Wittig Reaction for the Synthesis of 3,4-Dihydroquinazolines
Received date: 2023-11-08
Revised date: 2024-01-11
Online published: 2024-01-30
Supported by
Program for Science and Technology Development of Henan Province(212102310883)
A one-pot three-step synthesis for the preparation of 3,4-dihydroquinazolines is developed. This method involves a reductive amination of o-azidebenzaldehydes with amines followed by N-acylation using azoyl chloride and Staudinger/ intramolecular aza-Wittig sequence in the presence of P(Bu-n)3. Aromatic amines, benzylamines, and aliphatic chain amines could complete this multi-step reaction. The yield of butylamine, however, was slightly lower. Satisfactory yields can be obtained when aromatic acyl chloride containing electron-donating groups on the benzene ring was used. However, aromatic acyl chloride with electron withdrawing chlorine atoms and acryloyl chloride failed to give the corresponding products.
Wensheng Zhang , Wei Zheng , Guoqiang Zuo , Keyou Ma , Hequan Xiao , Gaiyun Liu . One-Pot Reductive Amination/N-Acylation/Aza-Wittig Reaction for the Synthesis of 3,4-Dihydroquinazolines[J]. Chinese Journal of Organic Chemistry, 2024 , 44(5) : 1686 -1690 . DOI: 10.6023/cjoc202311010
| [1] | (a) Patterson, S.; Alphey, M. S.; Jones, D. C.; Shanks, E. J.; Street, I. P.; Frearson, J. A.; Wyatt, P. G.; Gilbert, I. H.; Fairlamb, A. H. J. Med. Chem. 2011, 54, 6514. |
| [1] | (b) Thanigaimalai, P.; Lee, K.-C.; Bang, S.-C.; Lee, J.-H.; Yun, C.-Y.; Roh, E.; Hwang, B.-Y.; Kim, Y.; Jung, S.-H. Bioorg. Med. Chem. 2010, 18, 1555. |
| [1] | (c) Deepakumari, H. N.; Jayanna, B. K.; Prashanth, M. K.; Revanasiddappa, H. D.; Veeresh, B. Arch. Pharm. 2016, 349, 566. |
| [1] | (d) Dukat, M.; Alix, K.; Worsham, J.; Khatri, S.; Schulte, M. K. Bioorg. Med. Chem. Lett. 2013, 23, 5945. |
| [1] | (e) Seo, H. N.; Choi, J. Y.; Choe, Y. J.; Kim, Y.; Rhim, H.; Lee, S. H.; Kim, J.; Joo, D. J.; Lee, J. Y. Bioorg. Med. Chem. Lett. 2007, 17, 5740. |
| [1] | (f) Kang, H. B.; Rim, H.-K.; Park, J. Y.; Choi, H. W.; Choi, D. L.; Seo, J.-H.; Chung, K.-S.; Huh, G.; Kim, J.; Choo, D. J.; Lee, K.-T.; Lee, J. Y. Bioorg. Med. Chem. Lett. 2012, 22, 1198. |
| [1] | (g) Marschall, M.; Stamminger, T.; Urban, A.; Wildum, S.; Ruebsamen-Schaeff, H.; Zimmermann, H.; Lischka, P. Antimicrob. Agents Chemother. 2012, 56, 1135. |
| [1] | (h) Li, W.-J.; Li, Q.; Liu, D.-L.; Ding, M.-W. J. Agric. Food Chem. 2013, 61, 1419. |
| [1] | (i) Byun, J. S.; Sohn, J. M.; Leem, D. G.; Park, B.; Nam, J. H.; Shin, D. H.; Shin, J. S.; Kim, H. J.; Lee, K. T.; Lee, J. Y. Bioorg. Med. Chem. Lett. 2016, 26, 1073. |
| [1] | (j) Choi, D. L.; Jang, S. J.; Cho, S.; Choi, H. E.; Rim, H. K.; Lee, K. T.; Lee, J. Y. Bioorg. Med. Chem. Lett. 2014, 24, 1565. |
| [2] | Saito, T.; Tsuda, K.; Saito, Y. Tetrahedron Lett. 1996, 37, 209. |
| [3] | Dietrich, J.; Kaiser, C.; Meurice, N.; Hulme, C. Tetrahedron Lett. 2010, 51, 3951. |
| [4] | He, P.; Wu, J.; Nie, Y.-B.; Ding, M.-W. Eur. J. Org. Chem. 2010, 1088. |
| [5] | Song, A.; Marík, J.; Lam, K. S. Tetrahedron Lett. 2004, 45, 2727. |
| [6] | Zhong, Y.; Wang, L.; Ding, M.-W. Tetrahedron 2011, 67, 3714. |
| [7] | Kumar, R. A.; Saidulu, G.; Prasad, K. R.; Kumar, G. S.; Sridhar, B.; Reddy, K. R. Adv. Synth. Catal. 2012, 354, 2985. |
| [8] | Kumar, R. A.; Saidulu, G.; Sridhar, B.; Liu, S. T.; Reddy, K. R. J. Org. Chem. 2013, 78, 10240. |
| [9] | Xiong, J.; He, H.-T.; Yang, H.-Y.; Zeng, Z.-G.; Zhong, C.-R.; Shi, H.; Ouyang, M.-L.; Tao, Y.-Y.; Pang, Y.-L.; Zhang, Y.-H.; Hu, B.; Fu, Z.-X.; Miao, X.-L.; Zhu, H.-L. Yao, G. J. Org. Chem. 2022, 87, 9488. |
| [10] | Luo, L.-L.; Zhao, X.-L.; Zhang, L.; Yuan, Y.; Lü, S.-W.; Jia, X.-D. Tetrahedron 2016, 57, 5830. |
| [11] | Xiong, J.; Wei, X.; Yan, Y.-M.; Ding, M.-W. Tetrahedron 2017, 73, 5720. |
| [12] | Xiong, J.; Wei, X.; Wan, Y.-C.; Ding, M.-W. Tetrahedron 2019, 75, 1072. |
/
| 〈 |
|
〉 |
