Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy

被引：40

作者：

Zang, Qin ^{[1
]}

Javed, Salim ^{[1
,2
]}

Porubsky, Patrick ^{[3
]}

Ullah, Farman ^{[4
]}

Neuenswander, Benjamin ^{[3
]}

Lushington, Gerald H. ^{[1
,3
]}

Basha, Fatima Z. ^{[2
]}

Organ, Michael G. ^{[4
]}

Hanson, Paul R. ^{[1
,3
]}

机构：

[1] Univ Kansas, Dept Chem, Lawrence, KS 66045 USA

[2] Univ Karachi, Int Ctr Chem & Biol Sci, HEJ Res Inst Chem, Karachi 32, Pakistan

[3] Univ Kansas, Ctr Chem Methodol & Lib Dev KU CMLD, Del Shankel Struct Biol Ctr, Lawrence, KS 66047 USA

[4] York Univ, Dept Chem, Toronto, ON M3J 1P3, Canada

来源：

ACS COMBINATORIAL SCIENCE | 2012年 / 14卷 / 03期

基金：

美国国家科学基金会;

关键词：

isoindoline/tetrahydroisoquinoline; tricyclic sultam library; Heck-aza-Michael; COMPREHENSIVE SURVEY; CHEMICAL LIBRARIES; DRUG DISCOVERY; ONE-POT; BIOLOGY; 3-COMPONENT; LAUDANOSINE; ALKALOIDS; LIGANDS; SERIES;

D O I：

10.1021/co200181x

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing trycyclic sultam library, utilizing a Heck-aza-Michael (HaM) strategy is reported. Both isoindoline and THIQ rings are installed through a Heck reaction on a vinylsulfonamide, followed by one-pot deprotection and intramolecular aza-Michael reaction. Subsequent cycfization with either paraformaldehyde condensation or 1,1'-carbonyldiimidazole coupling generates a variety of tricyclic sultams. Overall, a 160-member library of these sultams, together with their isoindolines/THIQ and secondary sulfonamides precursors, were constructed using this strategy.

引用

页码：211 / 217

页数：7

共 51 条

[1] Application of a Sparse Matrix Design Strategy to the Synthesis of DOS Libraries [J].