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利用锅、原子和步骤经济性(PASE)合成构建八氢-4H-环戊并[b]吡啶-6-酮骨架。

Construction of Octahydro-4H-cyclopenta[b]pyridin-6-one Skeletons using Pot, Atom, and Step Economy (PASE) Synthesis.

作者信息

Raju Silver, Ghosh Palash, Nayani Kiranmai, Prashanth Jupally, Sridhar Balasubramanian, Mainkar Prathama S, Chandrasekhar Srivari

机构信息

Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, 500007, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India.

出版信息

Chemistry. 2023 Aug 21;29(47):e202301058. doi: 10.1002/chem.202301058. Epub 2023 Jul 28.

Abstract

Cascade aza-Piancatelli reaction and [3+3]/[4+2] cycloaddition reactions are carried out using the ideality principles of pot, atom, and step economy (PASE) synthesis. The reaction resulted in generation of octahydro-4H-cyclopenta[b]pyridin-6-one scaffolds. Moreover, octahydro-5,7a-epoxycyclopenta[cd]isoindol-4-one frameworks of gracilamine alkaloid and a novel decahydro-1H-dicyclopenta[cd,hi]isoindol-6-one were also realized in good yields with excellent regio- and diastereo-selectivities.

摘要

利用锅、原子和步骤经济性(PASE)合成的理想原则进行串联氮杂-皮安卡特利反应和[3+3]/[4+2]环加成反应。该反应生成了八氢-4H-环戊并[b]吡啶-6-酮骨架。此外,还以良好的产率、优异的区域和非对映选择性实现了格拉西拉明生物碱的八氢-5,7a-环氧环戊并[cd]异吲哚-4-酮骨架以及一种新型的十氢-1H-二环戊并[cd,hi]异吲哚-6-酮。

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