Stereoselective synthesis of benzosulfamidate-fused tetrahydroquinazoline scaffold via organocatalytic [4+2] cycloaddition of 2-amino-beta-nitrostyrenses of cyclic N-sulfimines

Sim Jong-Tack; Kim Hanna; Kim Sung-Gon

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Stereoselective synthesis of benzosulfamidate-fused tetrahydroquinazoline scaffold via organocatalytic [4+2] cycloaddition of 2-amino-beta-nitrostyrenses of cyclic N-sulfimines

机译：通过有机催化[4 + 2]环N-亚磺酰亚胺的2-氨基-β-硝基苯乙烯的有机加成[4 + 2]环加成，立体选择性地合成苯并磺酰胺酸盐稠合的四氢喹唑啉骨架

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A concise synthetic route to valuable highly functionalized benzosulfamidate-fused tetrahydroquinazoline is presented. The [4+2] cycloaddition of o-N-Cbz-amino-beta-nitrostyrene with benzoxathiazine 2,2-dioxide using an imidazole as the catalyst afforded tetrahydroquinazolines with high diastereoselectivities. Furthermore, a chiral quinine-derived squaramide organocatalyst promoted an asymmetric [4+2] cycloaddition reaction, providing enantioenriched benzosulfamidate-fused tetrahydroquinazolines with good enantiopurities (up to 69:31 er). (C) 2016 Elsevier Ltd. All rights reserved.

机译：提出了一种简明的合成路线，以合成有价值的高度官能化的苯氨基磺酰胺融合四氢喹唑啉。使用咪唑作为催化剂，将邻-N-Cbz-氨基-β-硝基苯乙烯与苯并恶嗪2，2-二氧化物进行[4 + 2]环加成反应，得到具有高非对映选择性的四氢喹唑啉。此外，手性奎宁衍生的方酰胺有机催化剂促进了不对称的[4 + 2]环加成反应，从而提供了对映体富集的苯并氨基氨基磺酸酯融合的四氢喹唑啉，具有良好的对映体纯度（可达69:31 er）。（C）2016 Elsevier Ltd.保留所有权利。

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《Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry》 |2016年第52期|共4页
作者
Sim Jong-Tack; Kim Hanna; Kim Sung-Gon;
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正文语种 eng
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Benzosulfamidate; Quinazoline; Cycloaddition reaction; Michael reaction; Organocatalyst;

机译：苯磺酰胺酸盐;喹唑啉;环加成反应;迈克尔反应;有机催化剂;

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1. Stereoselective synthesis of benzosulfamidate-fused tetrahydroquinazoline scaffold via organocatalytic [4+2] cycloaddition of 2-amino-beta-nitrostyrenses of cyclic N-sulfimines [J] . Sim Jong-Tack, Kim Hanna, Kim Sung-Gon Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2016,第52期

机译：通过有机催化[4 + 2]环N-亚磺酰亚胺的2-氨基-β-硝基苯乙烯的有机加成[4 + 2]环加成，立体选择性地合成苯并磺酰胺酸盐稠合的四氢喹唑啉骨架
2. Organocatalytic Asymmetric Mannich/Aza-Michael Cascade Reaction of delta-Formyl-alpha,beta-unsaturated Ketones with Cyclic N-Sulfimines: Enantioselective Synthesis of Benzosulfamidate-Fused Pyrrolidines [J] . Kim Hanna, Kim Yerin, Kim Sung-Gon The Journal of Organic Chemistry . 2017,第15期

机译：有机催化不对称Mannich / Aza-Michael级联反应δ-甲基-α，β-不饱和酮与环N-亚砜：苯并磺胺酰胺酰胺融合吡咯烷的对映选择性合成
3. Cycloaddition of gamma-Hydroxy-alpha,beta-unsaturated Ketones with Cyclic N-Sulfimines: Highly Stereoselective Synthesis of Polyheterotricyclic 1,3-Oxazolidine Derivatives [J] . Wang Jingjing, Li Feng, Shen Qin, Synthesis: International Journal of Methods in Synthetic Organic Chemistry . 2016,第3期

机译：γ-羟基-α，β-不饱和酮与环状N-亚磺酰亚胺的环加成反应：多杂环三环1,3-氧唑烷衍生物的高度立体选择性合成
4. ORGANOCATALYTIC STEREOSELECTIVE SYNTHESIS OF 2-DEOXYGLYCOSIDES [C] . Balmond E. I, Coe D. M., Galan M. C. International Carbohydrate Symposium . 2013

机译：有机催化立体选择合成2-脱氧糖苷
5. Intermolecular [5+2] cycloadditions: Novel five-atom components, serial [5+2]/[4+2] cycloadditions, and application to the synthesis of biologically active targets. [D] . Scanio, Marc Julian Charles. 2003

机译：分子间[5 + 2]环加成：新型五原子组分，系列[5 + 2] / [4 + 2]环加成及其在生物活性靶标合成中的应用。
6. Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double 3 + 2 dipolar cycloadditions followed by 5 + 1 annulation [O] . Xiaofeng Zhang, Kenny Pham, Shuai Liu, 2016

机译：通过一锅双3 + 2双极环加成然后进行5 +1环化立体选择性地合成稠合四氢喹唑啉
7. Stereoselective synthesis of fused tetrahydroquinazolines through one-pot double [3 + 2] dipolar cycloadditions followed by [5 + 1] annulation [O] . Xiaofeng Zhang, Kenny Pham, Shuai Liu, 2016

机译：立体选择性合成稠合四氢喹唑啉通过一锅双[3 + 2]偶极环加成，然后[5 + 1]环化

Stereoselective synthesis of benzosulfamidate-fused tetrahydroquinazoline scaffold via organocatalytic [4+2] cycloaddition of 2-amino-beta-nitrostyrenses of cyclic N-sulfimines

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