Solid‐Supported Synthesis

Barve, Indrajeet J.; Sun, Chung‐Ming

doi:10.1002/9781119288152.ch18

Cited by 2 publications

(1 citation statement)

References 62 publications

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“…During the last decades, solid-phase organic synthesis (SPOS) has become a powerful tool in rapid access to diverse compounds. In 1963, Merrifield introduced solid-phase peptide synthesis (SPPS) .…”

Section: Introductionmentioning

confidence: 99%

Greening Solid-Phase Organic Synthesis: Environmentally Conscious Synthesis of Pharmaceutically Relevant Privileged Structures 5,6-Dihydropyridin-2(1H)-ones and Quinolin-2(1H)-ones

et al. 2020

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Solid-phase organic synthesis (SPOS) is a very efficient methodology for the synthesis of diverse organic molecules, particularly exploited in drug discovery. Here, we present the transformation of the traditional SPOS to an ecofriendlier methodology on examples of pharmacologically relevant privileged structures 5,6-dihydropyridin-2(1H)-ones and quinolin-2(1H)-ones. The green approach is primarily based on the utilization of environmentally friendly solvent 2-MeTHF in all steps of the synthesis. Target heterocycles were synthesized by extending our previously published synthesis of five-membered tetramic acid analogues to six-membered cycles. The crucial step of the synthesis is cyclization via nonclassical Wittig olefination of resin-bound esters. Traditional and green protocols provided comparable results with respect to purity and yield of products, thus opening the way for greener access to a variety of diverse heterocycles.

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Section: Introductionmentioning

confidence: 99%