Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Felipe C. Demidoff; Eduardo José P. Rodrigues Filho; Andréa Luzia F. de Souza; Chaquip D. Netto; Leandro L. de Carvalho

doi:10.1055/s-0037-1610781

Synthesis, Table of Contents

Synthesis 2021; 53(21): 4097-4109
DOI: 10.1055/s-0037-1610781

paper

Cross-Coupling Reactions with 2-Amino-/Acetylamino-Substituted 3-Iodo-1,4-naphthoquinones: Convenient Synthesis of Novel Alkenyl- and Alkynylnaphthoquinones and Derivatives

Felipe C. Demidoff ∗

^aLaboratory of Chemistry, Federal University of Rio de Janeiro - Campus Macaé, Aluísio da Silva Gomes Avenue, 50, Granja dos Cavaleiros, 27930-560, Macaé, RJ, Brazil

,

Eduardo José P. Rodrigues Filho

^bLaboratory of Catalysis and Synthesis of Bioactive Substances (LACASB), Federal University of Rio de Janeiro–Campus Macaé, Imburo Road, No Number, Ajuda de Baixo, 27979-000, Macaé, RJ, Brazil

,

Andréa Luzia F. de Souza

^bLaboratory of Catalysis and Synthesis of Bioactive Substances (LACASB), Federal University of Rio de Janeiro–Campus Macaé, Imburo Road, No Number, Ajuda de Baixo, 27979-000, Macaé, RJ, Brazil

,

Chaquip D. Netto

^aLaboratory of Chemistry, Federal University of Rio de Janeiro - Campus Macaé, Aluísio da Silva Gomes Avenue, 50, Granja dos Cavaleiros, 27930-560, Macaé, RJ, Brazil

,

Leandro L. de Carvalho ∗

^bLaboratory of Catalysis and Synthesis of Bioactive Substances (LACASB), Federal University of Rio de Janeiro–Campus Macaé, Imburo Road, No Number, Ajuda de Baixo, 27979-000, Macaé, RJ, Brazil

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Abstract

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Abstract

Functionalized 1,4-naphthoquinones have been employed as versatile synthons in organic synthesis, in addition to presenting a large array of biological activities. Herein, the applications of 2-amino-/ acetylamino-substituted 3-iodo-1,4-naphthoquinones in cross-coupling reactions are described to successfully afford sixteen novel 3-styryl-1,4-naphthoquinones (amino-stilbene-quinone hybrids) and four 3-alkynyl-1,4-naphthoquinone in overall good yields. Interestingly, the alkynylated derivatives could be obtained from ligand- and Pd-free Cu^I-mediated cross-coupling reactions, after extensive investigations to exclude Pd as a co-catalyst. Lastly, the desilanized terminal alkyne was subjected to click chemistry reactions to give two novel triazole-1,4-naphthoquinone hybrids.

Key words

Castro–Stephens coupling - cycloaddition - Heck reaction - lithium chloride - Sonogashira reaction

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References

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