One-Pot Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Disubstituted Nicotinonitriles

Lin, Li-Chun; Suresh, S.; Lin, Kang; Kavala, Veerababurao; Yao, Ching‐Fa

doi:10.1021/acs.joc.3c00929

J. Org. Chem.

2023

DOI: 10.1021/acs.joc.3c00929

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One-Pot Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Disubstituted Nicotinonitriles

Li-Chun Lin

S. Suresh

Kang Lin

et al.

Abstract: We report on a copper-catalyzed three-component reaction for the synthesis of disubstituted nicotinonitriles using 3bromopropenals, benzoylacetonitriles, and ammonium acetate (NH 4 OAc). The Knoevenagel-type condensation of 3bromopropenals with benzoylacetonitriles gives δ-bromo-2,4-dienones that contain strategically placed functional groups that react with the ammonia generated in situ to give the corresponding azatrienes. These azatrienes can then be transformed into trisubstituted pyridines under the react… Show more

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Cited by 3 publications

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β‐halovinyl Aldehydes: Multifaceted Versatile Building Blocks In Organic Synthesis

Saini,

Jyoti,

Sharma

et al. 2024

Eur J Org Chem

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β‐halovinyl aldehydes serve as a valuable building blocks in organic synthesis. These aldo‐x bifunctional building blocks (AXB3s) contain a alkenic double bond (vinyl) as well as a formyl group along with a halogen atom (Cl, Br, I) bonded with the β‐carbon atom of vinyl aldehyde. Owing to the presence of these multiple reactive sites, β‐halovinyl aldehydes act as a suitable precursor for Michael addition, direct addition, cross‐coupling reactions, condensation reactions, nucleophilic substitution reactions, domino reactions, MCRs, Diels‐Alder reaction, functional group transformation reactions and enantioslective transformations. Therefore, a comprehensive review on synthetic exploration of β‐halovinyl aldehydes has been carried out for the generation of reactive intermediates and diverse bioactives heterocycles by using various C‐C, C‐N, C‐S and C‐O bond forming reactions. In this review, we have assembled the literature from mid‐2007 to Jan 2024.

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β‐halovinyl Aldehydes: Multifaceted Versatile Building Blocks In Organic Synthesis

Saini,

Jyoti,

Sharma

et al. 2024

Eur J Org Chem

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Synthesis of 2,3-Diperfluoroalkylated Quinoxalines via Selenium-Catalyzed Reductive C–C Coupling of Vicinal Perfluoroalkyl Formimidoyl Chlorides

Xiong,

Pu,

Xiao

et al. 2024

Org. Lett.

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A direct and efficient approach to access structurally interesting 2,3-diperfluoroalkylated quinoxalines via seleniumcatalyzed reductive C−C construction of vicinal bis(perfluoroalkyl formimidoyl chloride)s has been disclosed. This protocol features the use of easily accessible starting materials, scalability, and a diverse functional group tolerance. Mechanism studies suggested that this reaction may involve an interesting selenium-containing seven-membered-ring intermediate and proceed through an electrocyclization/selenium reductive elimination pathway, which is significantly different from the traditional transition-metal-catalyzed reductive coupling strategies of alkyl halides.Q uinoxalines are fundamental heterocyclic compounds that exist in many biologically active compounds and have wide applications in materials and medicine areas. 1 Quinoxaline derivatives find tremendous applications in materials science as dyes, cavitands, luminescent materials, etc. 2 Moreover, in the pharmaceutical area, quinoxaline medicines possess a variety of biological activities such as antitubercular, antibacterial, anticancer, antitumoral, antiinflammatory, antidepressant, anti-HIV, etc. (Figure 1). 3 Consequently, it is of great value to develop synthetic methods for the preparation of such important structural motifs. The most frequently utilized methodology for the synthesis of quinoxalines is the condensation or cyclization of o-phenylenediamines. In 1887, Hinsberg reported the first example of acid -catalyzed condensation of o-phenylenediamines and 1,2diketones to access quinoxalines. 4 However, this method requires high temperatures, long reaction times, and a strong acid catalyst. Subsequently, abundant analogues of 1,2diketones such as α-hydroxy ketones, α-halogenated ketones, epoxides, and 1,2-diol compounds were developed as synthetic blocks to construct quinoxalines by condensation with ophenylenediamines. 5 The synthesis of quinoxalines is also achieved through the use of transition metal catalysis 6 or hypervalent iodine(III)-or base/oxidant-mediated formal [4 + 2] annulation of alkynes with o-phenylenediamines. 7 In addition, the cyclization reaction between o-phenylenediamines and primary amines 8 and the dual protein cascade reaction using o-phenylenediamines, 1,2-diketones, and TsN 3 9

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One-Pot Synthesis of Disubstituted Nicotinonitriles

2024

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One-Pot Knoevenagel/Imination/6π-Azaelectrocyclization Sequence for the Synthesis of Disubstituted Nicotinonitriles

Cited by 3 publications

References 69 publications

β‐halovinyl Aldehydes: Multifaceted Versatile Building Blocks In Organic Synthesis

β‐halovinyl Aldehydes: Multifaceted Versatile Building Blocks In Organic Synthesis

Synthesis of 2,3-Diperfluoroalkylated Quinoxalines via Selenium-Catalyzed Reductive C–C Coupling of Vicinal Perfluoroalkyl Formimidoyl Chlorides

One-Pot Synthesis of Disubstituted Nicotinonitriles

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