Heck–Suzuki Tandem Reaction for the Synthesis of 3-Benzazepines

Peshkov, Anatoly A.; Peshkov, Vsevolod A.; Pereshivko, Olga P.; Hecke, Kristof Van; Kumar, Rakesh; Eycken, Erik V. Van der

doi:10.1021/acs.joc.5b00670

Cited by 36 publications

(21 citation statements)

References 35 publications

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“…In our route (Scheme 2), the synthesis of the precursor of (5), compound (4), from arylboronic acid (2) and (Z)-methyl-2-iodo-3-methoxyacrylate (3) 11 depended on Suzuki-Miyaura cross-coupling reaction as the crucial step. 12,13 Optimum reaction conditions should be selected in order to obtain the highest yield. Table 1 records the effects of different mole ratios of reactants on the yield of compound (4).…”

Section: Resultsmentioning

confidence: 99%

A Concise Synthesis of Azoxystrobin using a Suzuki Cross-Coupling Reaction

Liu

Luo

2015

Journal of Chemical Research

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Section: Resultsmentioning

confidence: 99%

A Concise Synthesis of Azoxystrobin using a Suzuki Cross-Coupling Reaction

Liu

Luo

2015

Journal of Chemical Research

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“…In 2014, Van der Eycken and co-workers 89 disclosed the synthesis of ,-unsaturated -lactams 201 via a one-pot Ugi-4CR followed by 5-endo-dig carbocyclization and retro-Claisen fragmentation at 80 °C (Scheme 46). The authors used 3-substituted propiolic acids and phenyl glyoxals along with different amines and isocyanides to give Ugi adducts 199.…”

Section: -Unsaturated -Lactamsmentioning

confidence: 99%

Synthesis of Lactams via Isocyanide-Based Multicomponent Reactions

Pharande¹

2020

Synthesis

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Lactams are very important heterocycles as a result of their presence in a wide range of bioactive molecules, natural products and drugs, and also due their utility as versatile synthetic intermediates. Due to these reasons, numerous efforts have focused on the development of effective and efficient methods for their synthesis. Compared to conventional two-component reactions, multicomponent reactions (MCRs), particularly isocyanide-based MCRs, are widely used for the synthesis of a range of small heterocycles including lactam analogues. Despite their numerous applications in almost every field of chemistry, as yet there is no dedicated review on isocyanide-based multicomponent reactions (IMCRs) concerning the synthesis of lactams. Therefore, this review presents strategies towards the synthesis of α-, β-, γ-, δ- and ε-lactams using IMCRs or IMCRs/post-transformation reactions reported in the literature between 2000 and 2020.1 Introduction2 Developments in Lactam Synthesis2.1 α-Lactams2.2 β-Lactams2.3 γ-Lactams2.3.1 General γ-Lactams2.3.2 Benzo-Fused γ-Lactams2.3.3 Spiro γ-Lactams2.3.4 α,β-Unsaturated γ-Lactams2.3.5 Polycyclic Fused γ-Lactams2.4 δ-Lactams2.5 ε-Lactams3 Conclusions

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“…Starting from propargylamide 99 , a novel protocol for the tandem Heck–Suzuki reaction was used for the construction of the benzoazocines 100 and 101 (Scheme 31 ). 42…”

Section: Heck Reactionmentioning

confidence: 99%