Synthesis, Table of Contents Synthesis 2025; 57(13): 2075-2082DOI: 10.1055/a-2567-4696 paper Stereoselective Synthesis of Benzosultam-Fused Tetrahydroquinazolines via [4+2]-Cycloaddition of Cyclic N-Sulfonyl Ketimines with 2-Aminophenyl Enones Authors Ji Won Han Sung-Gon Kim∗ Recommend Article Abstract Buy Article(opens in new window) All articles of this category(opens in new window) Abstract A [4+2]-cycloaddition reaction between cyclic N-sulfonyl ketimines and 2-aminophenyl enones, catalyzed by K2CO3, has been developed. This method provides a straightforward and efficient approach for synthesizing a wide range of structurally complex and highly functionalized benzosultam-fused tetrahydroquinazolines in high yields, with excellent diastereoselectivities. Key words Key words[4+2]-cycloaddition - benzosultams - 2-aminophenyl enones - cyclic N-sulfonyl ketimines - tetrahydroquinazolines Full Text References References 1a Wrobe J, Dietrich A, Woolson SA, Millen J, McCaleb M, Harrison MC, Hohman TC, Sredy J, Sullivan D. J. Med. Chem. 1992; 35: 4613 1b Wells GJ, Tao M, Josef KA, Bihovsky R. J. Med. Chem. 2001; 44: 3488 1c Takeuchi Y, Liu Z. Heterocycles 2002; 56: 693 1d Jakopin Ž, Gobec M, Mlinarič-Raščan I, Dolenc MS. J. Med. Chem. 2012; 55: 6478 1e Zhang S, Li L, Hu Y, Zha Z, Wang Z, Loh TP. Org. Lett. 2015; 17: 1050 2a Ahn KH, Kim SK, Ham C. Tetrahedron Lett. 1998; 39: 6321 2b Rast S, Modec B, Stephan M, Mohar B. Org. Biomol. Chem. 2016; 14: 2112 2c Cotman AE, Lozinšek M, Wang B, Stephan M, Mohar B. Org. Lett. 2019; 21: 3644 2d Hašanova S, Cingl J, Tomašič T, Cotman AE. Tetrahedron Lett. 2024; 138: 154984 For reviews on benzosultams, see: 3a Majumdar KC, Mondal S. Chem. Rev. 2011; 111: 7749 3b Zhao Q.-Q, Hu X.-Q. Molecules 2020; 25: 4367 4a Han JW, Kim Y, Kim S.-G. Org. Lett. 2024; 26: 252 4b Kim Y, Kim Y, Kim S.-G. Chem. Asian J. 2024; 19: e202301011 5 For a review on cyclic N-sulfonyl ketimines, see: Guin S, Majee D, Samanta S. Chem. Commun. 2021; 57: 9010 For examples of [4+2]-cycloaddition using cyclic N-sulfonyl ketimines, see: 6a Takizawa S, Arteaga FA, Yoshida Y, Suzuki M, Sasai H. Asian J. Org. Chem. 2014; 3: 412 6b Zheng PC, Cheng J, Su S, Jin Z, Wang Y.-H, Yang S, Jin L.-H, Song BA, Chi YR. Chem. Eur. J. 2015; 21: 9984 6c Wang X, Lu M, Su Q, Zhou M, Addepalli Y, Yao W, Wang Z, Lu Y. Chem. Asian J. 2019; 14: 3409 6d Li T, Xiao H, Renjun X, Wang J, Luo Y, Wang Q, Wu S, Zheng P. Org. Lett. 2023; 25: 688 For examples of cycloaddition of nonprotected 2-aminophenyl enones, see: 7a Jia Z.-X, Luo Y.-C, Wang Y, Chen L, Xu P.-F, Wang B. Chem. Eur. J. 2012; 18: 12958 7b Zhang H.-R, Dong Z.-W, Yang Y.-J, Wang P.-L, Hui X.-P. Org. Lett. 2013; 15: 4750 7c Yang J, Ke C, Zhang D, Liu X, Feng X. Org. Lett. 2018; 20: 4536 8 Yan W, Wang D, Feng J, Li P, Zhao D, Wang R. Org. Lett. 2012; 14: 2512 9 Park DY, Lee SY, Jeon J, Cheon C.-H. J. Org. Chem. 2018; 83: 12486 Supplementary Material Supplementary Material Supporting Information (PDF)
