Photomediated One-Pot Multicomponent Cascade Reaction for the Synthesis of N-Acyl/Sulfonyl-α-Phosphonated-1,2,3,4-Tetrahydroisoquinoline via Twice Acyl/Sulfonyl Iminium Formation

被引：0

作者：

Zhang, Yun ^{[1
,2
,3
]}

Nie, Jia-Huan ^{[1
,2
,3
]}

Du, Yao ^{[1
,2
,3
]}

Ye, Xin-Rui ^{[1
,2
,3
]}

Cui, Bao-Dong ^{[1
,2
,3
]}

Mou, Xue-Qing ^{[1
,2
,3
]}

Liu, Jia-Bao ^{[4
]}

Yuan, Wei-Cheng ^{[1
,5
]}

Chen, Yong-Zheng ^{[1
,2
,3
]}

机构：

[1] Zunyi Med Univ, Sch Pharm, Green Pharmaceut Engn Res Ctr Guizhou Prov, Key Lab Biocatalysis & Chiral Drug Synth Guizhou P, Zunyi 563006, Peoples R China

[2] Zunyi Med Univ, Key Lab Basic Pharmacol, Minist Educ, Zunyi 563006, Peoples R China

[3] Zunyi Med Univ, Minist Educ, Joint Int Res Lab Ethnomed, Zunyi 563006, Peoples R China

[4] Univ Toronto, Donnelly Ctr Cellular & Biomol Res, Toronto, ON M5S 3E1, Canada

[5] Chengdu Univ, Inst Adv Study, Res Ctr Chiral Drugs, Chengdu 610106, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2025年 / 20卷 / 09期

关键词：

1-Phosphonated N-acyl/sulfonyl 1,2,3,4-tetrahydroisoquinolines; Photomediated redox; One-pot multicomponent cascade reaction; Twice acyl/sulfonyl iminium intermediate strategy; AMINOPHOSPHONIC ACIDS; ASYMMETRIC-SYNTHESIS; HETEROCYCLES; DESIGN; ROUTE;

D O I：

10.1002/asia.202401542

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

N-acyl/sulfonyl-alpha-phosphonated 1,2,3,4-tetrahydroiso-quinolines (THIQs) are significant structural motifs in organic synthesis and drug discovery. However, the one-pot approach enabling direct difunctionalization of THIQs remains challenging. Herein we report a photomediated one-pot multicomponent cascade reaction to access N-acyl/sulfonyl-alpha-phosphonated THIQs via twice acyl/sulfonyl iminium. This method features air as an oxidant, high atom and step economy, and mild conditions.

引用

页数：5

共 47 条

[1] Porphyrins as Catalysts in Scalable Organic Reactions [J].

Barona-Castano, Juan C. ;

Carmona-Vargas, Christian C. ;

Brocksom, Timothy J. ;

de Oliveira, Kleber T. .

MOLECULES, 2016, 21 (03)

[2] α-Sulfonamidophosphonates as new anti-mycobacterial chemotypes: Design, development of synthetic methodology, and biological evaluation [J].

Bhagat, Srikant ;

Supriya, Metheku ;

Pathak, Satish ;

Sriram, Dharmarajan ;

Chakraborti, Asit K. .

BIOORGANIC CHEMISTRY, 2019, 82 :246-252

[3] Discovery of Potent and Orally Bioavailable Macrocyclic Peptide-Peptoid Hybrid CXCR7 Modulators [J].

Boehm, Markus ;

Beaumont, Kevin ;

Jones, Rhys ;

Kalgutkar, Amit S. ;

Zhang, Liying ;

Atkinson, Karen ;

Bai, Guoyun ;

Brown, Janice A. ;

Eng, Heather ;

Goetz, Gilles H. ;

Holder, Brian R. ;

Khunte, Bhagyashree ;

Lazzaro, Sarah ;

Limberakis, Chris ;

Ryu, Sangwoo ;

Shapiro, Michael J. ;

Tylaska, Laurie ;

Yan, Jiangli ;

Turner, Rushia ;

Leung, Siegfried S. F. ;

Ramaseshan, Mahesh ;

Price, David A. ;

Liras, Spiros ;

Jacobson, Matthew P. ;

Earp, David J. ;

Lokey, R. Scott ;

Mathiowetz, Alan M. ;

Menhaji-Klotz, Elnaz .

JOURNAL OF MEDICINAL CHEMISTRY, 2017, 60 (23) :9653-9663

[4] Dioncophylline A as a growth-retarding agent against the herbivorous insect Spodoptera littoralis: Structure-activity relationships [J].

Bringmann, G ;

Holenz, J ;

Wiesen, B ;

Nugroho, BW ;

Proksch, P .

JOURNAL OF NATURAL PRODUCTS, 1997, 60 (04) :342-347

[5] Gentrymine B, an N-quaternary Ancistrocladus alkaloid:: Stereoanalysis, synthesis, and biomimetic formation from gentrymine A [J].

Bringmann, G ;

Ochse, M ;

Michel, M .

TETRAHEDRON, 2000, 56 (04) :581-585

[6] Selection of DNA-Encoded Libraries to Protein Targets within and on Living Cells [J].

Cai, Bo ;

Kim, Dongwook ;

Akhand, Saeed ;

Sun, Yixing ;

Cassell, Robert J. ;

Alpsoy, Aktan ;

Dykhuizen, Emily C. ;

Van Rijn, Richard M. ;

Wendt, Michael K. ;

Krusemark, Casey J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (43) :17057-17061

[7] Enantioselective dearomatization of isoquinolines by anion-binding catalysis en route to cyclic α-aminophosphonates [J].

Choudhury, Abhijnan Ray ;

Mukherjee, Santanu .

CHEMICAL SCIENCE, 2016, 7 (12) :6940-6945

[8] Asymmetric Synthesis of Isoquinoline Alkaloids: 2004-2015 [J].

Chrzanowska, Maria ;

Grajewska, Agnieszka ;

Rozwadowska, Maria D. .

CHEMICAL REVIEWS, 2016, 116 (19) :12369-12465

[9] Recent applications of porphyrins as photocatalysts in organic synthesis: batch and continuous flow approaches [J].

Costa e Silva, Rodrigo ;

da Silva, Luely Oliveira ;

Bartolomeu, Aloisio de Andrade ;

Brocksom, Timothy John ;

de Oliveira, Kleber Thiago .

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 :917-955

[10] Design, Synthesis, and Biological Evaluation of Erythrina Alkaloid Analogues as Neuronal Nicotinic Acetylcholine Receptor Antagonists [J].

Crestey, Francois ;

Jensen, Anders A. ;

Borch, Morten ;

Andreasen, Jesper Tobias ;

Andersen, Jacob ;

Balle, Thomas ;

Kristensen, Jesper Langgaard .

JOURNAL OF MEDICINAL CHEMISTRY, 2013, 56 (23) :9673-9682

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