Multicomponent synthesis of epoxy-tetrahydronaphthyridine and structural diversification by subsequent fragmentation

Fayol, Aude

doi:10.1016/j.tet.2005.09.017

Cited by 16 publications

(4 citation statements)

References 46 publications

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“…It is worth noting that one C−N, one C−O, and three C−C bonds were formed with concomitant creation of five asymmetric centers in this one-pot multicomponent process. Compound 810a is readily fragmented to pyrrolo[3,4- b ]pyridine 811a , while 810b gave 5,6,7,8-tetrahydro-1,7-naphthyridines 811b in good yields after acidic treatment (Scheme ).…”

Section: Multicomponent Reactions Of Isocyanoacetates and Isocyanoace...mentioning

confidence: 99%

Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application

et al. 2010

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Section: Multicomponent Reactions Of Isocyanoacetates and Isocyanoace...mentioning

confidence: 99%

Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application

et al. 2010

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“…The dienophile is introduced, either as part of one of the starting materials of the Ugi condensation, usually the amine component, or incorporated as external reagent. This approach has been used for synthesis of different heterocycles and other complex compounds, such as pyrrolopyridines ( 103 ) [ 31 ], hexasubstituted benzenes ( 104 ) [ 32 ], tetrahydroquinolines ( 105 ) [ 33 ], phenantrolines ( 106 ) [ 34 ], polycyclic natural product-like scaffolds ( 107 ) [ 35 ], furoquinolines ( 108 ) [ 36 ], tetrahydrofuropyridines ( 109 ) [ 37 ], and naphthyridines ( 110 ) [ 38 ] (Fig. 1 ).…”

Section: Synthesis Of Heterocycles From Bifunctional Isocyanidesmentioning

confidence: 99%

Stefano Marcaccini: a pioneer in isocyanide chemistry

et al. 2023

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Stefano Marcaccini was one of the pioneers in the use of isocyanide-based multicomponent reactions in organic synthesis. Throughout his career at the University of Florence he explored many different faces of isocyanide chemistry, especially those geared towards the synthesis of biologically relevant heterocycles. His work inspired many researchers who contributed to other important developments in the field of multicomponent reactions and created a school of synthetic chemists that continues today. In this manuscript we intend to review the articles on isocyanide multicomponent reactions published by Dr. Marcaccini and analyse their influence on the following works by other researchers. With this, we hope to highlight the immense contribution of Stefano Marcaccini to the development of isocyanide chemistry and modern organic synthesis as well as the influence of his research on future generations. We believe that this review will not only be a well-deserved tribute to the figure of Stefano Marcaccini, but will also serve as a useful inspiration for chemists working in this field. Graphical abstract

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“…In this way, the use of a-acetamidoisocyanides in Ugi reactions yields highly substituted oxazoles which in situ react intramolecularly to afford complex heterocyclic systems and cyclodepsipeptides, thereby leading to broad scaffold diversity. [51] In a related approach, Schreiber reported examples of diversity-oriented syntheses using furan-containing Ugi and Passerini adducts, which are subsequently transformed in a flexible manner (Scheme 27). [52]…”

Section: Isocyanide-based Reactionsmentioning

confidence: 99%

Heterocycles as Key Substrates in Multicomponent Reactions: The Fast Lane towards Molecular Complexity

Isambert

Lavilla

2008

Chemistry A European J

309

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Heterocycles display an intrinsic reactivity which enables rich, versatile and productive transformations. Taking into account their ubiquitous presence in natural products and drugs, the development of new, fast and efficient preparative protocols for these structures remains an urgent task in Organic Synthesis. Multicomponent reactions using heterocyclic chemistry offer new possibilities to exploit this exclusive reactivity. Recent results show relevant examples of such transformations. Several approaches which allow the construction of complex heterocyclic compounds from simple starting materials using this principle have been analyzed.

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Multicomponent synthesis of epoxy-tetrahydronaphthyridine and structural diversification by subsequent fragmentation

Cited by 16 publications

References 46 publications

Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application

Isocyanoacetate Derivatives: Synthesis, Reactivity, and Application

Stefano Marcaccini: a pioneer in isocyanide chemistry

Heterocycles as Key Substrates in Multicomponent Reactions: The Fast Lane towards Molecular Complexity

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