Synthesis of a Unique Isoindoline/Tetrahydroisoquinoline-based Tricyclic Sultam Library Utilizing a Heck-aza-Michael Strategy
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- 作者：Qin Zang ; Salim Javed ; Patrick Porubsky ; Farman Ullah ; Benjamin Neuenswander ; Gerald H. Lushington ; Fatima Z. Basha ; Michael G. Organ ; Paul R. Hanson
- 刊名：ACS Combinatorial Science
- 出版年：2012
- 出版时间：March 12, 2012
- 年：2012
- 卷：14
- 期：3
- 页码：211-217
- 全文大小：454K
- 年卷期：v.14,no.3(March 12, 2012)
- ISSN：2156-8944
文摘
The synthesis of a unique isoindoline- and tetrahydroisoquinoline (THIQ)-containing tricyclic 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 cyclization with either paraformaldehyde condensation or 1,1鈥?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.