Palladium-catalysed aminocarbonylation/cyclization of iodoalkenes toward N-propargylcarboxamides and oxazoles

Szuroczki, Péter; Mikle, Gábor; Kollár, László

doi:10.1016/j.mcat.2018.03.015

Cited by 6 publications

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“…Based on our preliminary investigations with similar iodoalkene functionalities, i.e., their use in aminocarbonylation/cyclization sequence to obtain oxazoles (Szuroczki et al 2018), as well as in asymmetric aminocarbonylation to obtain diastereoisomers of various carboxamides (Mikle 2017), a systematic investigation regarding the structure of both substrate and N-nucleophile was decided. In the present paper, a facile procedure for the synthesis of 20-carboxamidopregnenes is described using the 20-keto-20-hydrazone-20-iodo-20-ene-20-carboxamido-20-ene reaction pathway.…”

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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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confidence: 99%

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

et al. 2021

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Synthesis of 2‐Methylresorcinol‐Based Deepened Cavitands with Chiral Inlet Bearing Steroidal Moieties on the Upper Rim

et al. 2020

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A tetraiodocavitand, synthesised in conventional high‐yielding reactions, was used as substrate in homogeneous catalytic reactions such as aminocarbonylation and Sonogashira reaction. 3α‐Aminopregnane and 17α‐ethinylandrostane derivatives were used as coupling agents, respectively. While the aminocarbonylation of the tetraiodocavitand carried out at low pressure carbon monoxide resulted in the formation of tetra‐carboxamides as major products, the high pressure carbonylation (40 bar CO) yielded the corresponding tetrakis(2‐ketocarboxamides) with high chemoselectivity. The ethinyl functionality of the steroid enabled the facile cross‐coupling with the cavitand possessing iodoarene functionalities.

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Recent advances in polymer supported palladium complexes as (nano)catalysts for Sonogashira coupling reaction

Nasrollahzadeh

Motahharifar

Ghorbannezhad

et al. 2020

Molecular Catalysis

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Palladium-catalysed aminocarbonylation/cyclization of iodoalkenes toward N-propargylcarboxamides and oxazoles

Cited by 6 publications

References 67 publications

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

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

Synthesis of 2‐Methylresorcinol‐Based Deepened Cavitands with Chiral Inlet Bearing Steroidal Moieties on the Upper Rim

Recent advances in polymer supported palladium complexes as (nano)catalysts for Sonogashira coupling reaction

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