Green solvents for the formation of amide linkages

Procopio, Debora; Siciliano, Carlo; Trombino, Sonia; Dumitrescu, Dan; Felicia, Suciu; Gioia, Maria Luisa Di

doi:10.1039/d1ob01814k

Cited by 31 publications

(23 citation statements)

References 118 publications

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“…Furthermore, existing amidation protocols in organic solvents are not ideal alternatives either, as these protocols often use hazardous and unsustainable solvents such as dimethylformamide, N -methylpyrrolidon, or dichloromethane. The use of these solvents is currently considered one of the main issues in amidation reactions, emphasizing the importance of the use of alternative, greener solvents [ 6 ].…”

Section: Introductionmentioning

confidence: 99%

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

2022

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Phenol amides are bioactive compounds naturally present in many plants. This class of compounds is known for antioxidant, anti-inflammatory, and anticancer activities. To better understand the reactivity and structure–bioactivity relationships of phenol amides, a large set of structurally diverse pure compounds are needed, however purification from plants is inefficient and laborious. Existing syntheses require multiple steps, including protection of functional groups and are generally overly complicated and only suitable for specific combinations of hydroxycinnamic acid and amine. Thus, to facilitate further studies on these promising compounds, we aimed to develop a facile general synthetic route to obtain phenol amides with a wide structural diversity. The result is a protocol for straightforward one-pot synthesis of phenol amides at room temperature within 25 h using equimolar amounts of N,N′-dicyclohexylcarbodiimide (DCC), amine, hydroxycinnamic acid, and sodium bicarbonate in aqueous acetone. Eight structurally diverse phenol amides were synthesized and fully chemically characterized. The facile synthetic route described in this work is suitable for a wide variety of biologically relevant phenol amides, consisting of different hydroxycinnamic acid subunits (coumaric acid, ferulic acid, and sinapic acid) and amine subunits (agmatine, anthranilic acid, putrescine, serotonin, tyramine, and tryptamine) with yields ranging between 14% and 24%.

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Section: Introductionmentioning

confidence: 99%

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

2022

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“…To sum up, Cyrene seems to be a plausible solvent for peptide chemistry, but further research ought to be done, considering the synthesis of larger peptides and their purification. 35…”

Section: Cyrene In Organic Chemistrymentioning

confidence: 99%

Cyrene: a bio-based novel and sustainable solvent for organic synthesis

2022

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“…A formação de ligações amida está entre as mais realizadas em indústrias químicas e farmacêuticas (PROCOPIO et al, 2022). Devido à sua grande aplicação, principalmente para produção de medicamentos, diversos métodos são estudados para sua obtenção (NI et al, 2022).…”

Section: Proposta De Mudança Da Rota De Sínteseunclassified

Minimização De Deslocamento De Operadores Por Meio De Agrupamento De Ferramentais Em Arranjos Físicos Posicionais

Shih¹

2022

Engenharias: Criação E Repasse De Tecnologias 3

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Direitos para esta edição cedidos à Atena Editora pelos autores. Open access publication by Atena Editora Todo o conteúdo deste livro está licenciado sob uma Licença de Atribuição Creative Commons. Atribuição-Não-Comercial-NãoDerivativos 4.0 Internacional (CC BY-NC-ND 4.0). O conteúdo dos artigos e seus dados em sua forma, correção e confiabilidade são de responsabilidade exclusiva dos autores, inclusive não representam necessariamente a posição oficial da Atena Editora. Permitido o download da obra e o compartilhamento desde que sejam atribuídos créditos aos autores, mas sem a possibilidade de alterá-la de nenhuma forma ou utilizá-la para fins comerciais.Todos os manuscritos foram previamente submetidos à avaliação cega pelos pares, membros do Conselho Editorial desta Editora, tendo sido aprovados para a publicação com base em critérios de neutralidade e imparcialidade acadêmica.A Atena Editora é comprometida em garantir a integridade editorial em todas as etapas do processo de publicação, evitando plágio, dados ou resultados fraudulentos e impedindo que interesses financeiros comprometam os padrões éticos da publicação. Situações suspeitas de má conduta científica serão investigadas sob o mais alto padrão de rigor acadêmico e ético.

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Green solvents for the formation of amide linkages

Abstract: Green solvents as alternatives for cleaner and safer amide synthesis.

Cited by 31 publications

References 118 publications

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

Facile Amidation of Non-Protected Hydroxycinnamic Acids for the Synthesis of Natural Phenol Amides

Cyrene: a bio-based novel and sustainable solvent for organic synthesis

Minimização De Deslocamento De Operadores Por Meio De Agrupamento De Ferramentais Em Arranjos Físicos Posicionais

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