Catalyst-Free, Room-Temperature Accessible Regioselective Synthesis of Spiroquinolines and Their Antioxidant Study

ACS Omega. 2022 Dec 19;8(1):444-456. doi: 10.1021/acsomega.2c05020. eCollection 2023 Jan 10.

ABSTRACT

An efficient, regioselective, and environmentally benign approach was established using the multicomponent reaction-based synthesis of novel antioxidant spiroquinoline derivatives such as spiro[dioxolo[4,5-g]quinoline], spiro[dioxino[2,3-g]quinoline], and spiro[pyrazolo[4,3-f]quinoline] by reaction of aryl aldehyde, Meldrum’s acid, and amine derivatives under an additive-free reaction in aqueous ethanol. Here, two asymmetric carbon centers, three new C-C bonds, and one C-N bond are developed in the final motif. This synthetic methodology offers excellent yields with an easy workup procedure, high diastereoselectivity [d.r. >50:1 (cis/trans)], admirable atom economy, and low E-factor values. Synthesized spiro compounds were investigated for their in vitro antioxidant activity by 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) and 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical scavenging assays. In the ABTS radical scavenging assay, compounds 4d, 4f, and 4l exhibit excellent potency, and in the DPPH radical scavenging assay, compounds 4a, 4d, 4f, and 4g, exhibit excellent potency.

PMID:36643529 | PMC:PMC9835643 | DOI:10.1021/acsomega.2c05020

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