Facile, High-Yielding Synthesis of Steroidal Crown Ethers via Palladium-Catalyzed Carbonylation Reaction

Petz, Andrea; Gálik, György; Horváth, Judit; Tuba, Zoltán; Berente, Zoltán; Pintér, Zoltán; Kollár, László

doi:10.1081/scc-100000521

Cited by 19 publications

(6 citation statements)

References 12 publications

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“…17-Iodo-androsta-16-enes were employed as substrates in aminocarbonylation with crown-ethers possessing an aminomethyl group (Figure 15). Excellent yields were reported regardless of the size of the crown-ether moiety [75]. In Pd-catalyzed carbonylation reactions,12-carboxamido-and 12-carboxyl-11-spirostenes were synthesized from the corresponding 12-iodo-11-ene derivative under mild conditions (Figure 16).…”

Section: Preparation Of Carbonyl Compounds With Steroid Scaffoldsmentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a vast number of applications for the synthesis of simple building blocks as well as for the functionalization of biologically important skeletons. This review covers the history of carbonylative coupling reactions in Hungary between the years 1994 and 2021.

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Section: Preparation Of Carbonyl Compounds With Steroid Scaffoldsmentioning

confidence: 99%

27 Years of Catalytic Carbonylative Coupling Reactions in Hungary (1994–2021)

2022

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“…The introduction of an amide functionality in steroidal substrates via palladium-catalysed aminocarbonylation, especially into the most distinguished position-3 and -17 (in ring A and D, respectively), has long been the aim of the patent literature as well (Holt et al 1989Cacchi et al 1986;Dolle et al 1987;Tian et al 2000;McGuire et al 1998;Petz et al 2001). Efforts have been made also for the synthesis of 11-and 12-carboxamides using the same methodology, i.e., aminocarbonylation of the corresponding iodoalkene functionalities in the most hindered positions (Ács et al 2006, 2007).…”

Section: ) Provided a Solidmentioning

confidence: 99%

Synthesis of novel pregnane-based 20-carboxamides via palladium-catalysed aminocarbonylation

et al. 2021

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Abstract20-Carboxamidopregnene derivatives, such as 3β-acetoxy-5α-pregn-20-ene-20-carboxamides and 5α-pregn-20-ene-20-carboxamides were synthesized from the widely accessible 3β-acetoxy-pregn-5,16-dien-20-one (PDA) using selective hydrogenation, hydrazine and iodoalkene formation, as well as palladium-catalysed aminocarbonylation. The 20-iodo-20-ene derivatives, obtained from the corresponding 20-keto derivatives via their hydrazones, served as substrates. 23 new 20-carboxamides were obtained using various N-nucleophiles ranging from simple primary amines to α-amino acid esters. The novelty of this methodology lies in the application of facile, moderate or high-yielding reactions to obtain otherwise hardly accessible steroidal 20-carboxamides of pharmaceutical importance. In other words, instead of the enzymatic or synthetic degradation of e.g., sterols or cholanic acids, functionalization of the basic skeleton (a ‘building-up’ approach) was used.

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“…129 17-Carboxamido-androstanes possessing crown ether moieties attached to the amide functionality were synthesized from the corresponding 17-iodo-androst-16-enes. 130 Various steroidal hydrazides [131][132][133] and hydroxamic acid derivatives 134,135 were obtained by aminocarbonylation reactions using mono-or disubstituted hydrazines and either N-or O-substituted hydroxylamines as nucleophiles. As mentioned before, these reactions can be regarded as the acylation of the nucleophiles by the acylpalladium complex formed by consecutive oxidative addition-CO insertion reactions.…”

Section: Aminocarbonylation and Related Reactionsmentioning

confidence: 99%