Highly Substituted Medium-Sized Ring-Fused Azocinoquinoline Scaffolds by Post-Ugi-4CR Reductive Carbopalladation Cyclization

Ghazvini, Helya Janatian; Müller, Thomas J. J.; Röminger, Frank; Balalaie, Saeed

doi:10.1021/acs.joc.9b01269

Cited by 18 publications

(4 citation statements)

References 40 publications

(34 reference statements)

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“…In 2019, Balalaie reported an efficient method to highly functionalized azocinoquinolines with good regio‐ and diastereoselectivity via a palladium‐catalyzed post‐Ugi reductive carbopalladation (Scheme 13). [18] The electron‐donating effect of the quinoline core and the stability of the 8‐membered ring compared to a 9‐membered ring favor this regioselectivity. According to the control studies, structure C supports a syn ‐carbopalladation‐hydride capture sequence ( D ) occurring in an 8‐ exo ‐dig fashion resulting in a single diastereomer.…”

Section: Cyclic Peptidomimeticsmentioning

confidence: 99%

Recent Advances in the Synthesis of Peptidomimetics via Ugi Reactions

Liu,

Voskressensky,

Van der Eycken

2024

Chemistry A European J

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Peptidomimetics have been extensively explored in many area due to their ability to improve pharmacological qualities and interesting biological activities. Cycles could be incorporated in peptides to reduce their flexibility, often enhancing the affinity for a certain receptor. Many efforts have been made to synthesize various peptidomimetics. Among them, the Ugi reaction is a popular way for the synthesis of peptidomimetics because it provides peptide‐like products. The Ugi reaction consists of the condensation of an aldehyde or ketone, a carboxylic acid, an amine, and an isocyanide usually giving a linear peptidomimetic. In order to obtain other linear, cyclic or polycyclic peptidomimetics, the acyclic products have to undergo additional transformations or cyclizations. This review covers the years from 2018‐2023, regarding the synthesis of linear, cyclic and polycyclic peptidomimetics, employing Ugi reactions eventually followed by post‐Ugi transformations. Organo‐catalyzed reactions, base‐promoted reactions, and metal‐free reactions toward peptidomimetics are highlighted.

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Section: Cyclic Peptidomimeticsmentioning

confidence: 99%

Recent Advances in the Synthesis of Peptidomimetics via Ugi Reactions

Liu,

Voskressensky,

Van der Eycken

2024

Chemistry A European J

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“…In an fascinating research, 2‐ dihydroazocino[4,3‐ b ]quinolin‐3‐ones 302 synthesized through post‐Ugi transformation reaction [185] . This this approach, reductive cyclo‐carbopalladation of Ugi‐4CR compound considered as a key step leads to the azocinoquinolines (Scheme 94).…”

Section: Fused Homo/heterocyclic To the Quinoline Scaffoldmentioning

confidence: 99%

Recent Advances in the Synthesis of Fused‐Cyclic Quinolines

Darbandizadeh,

Balalaie

2024

Asian J Org Chem

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Fused quinolines have gained substantial attention due to their significant biological and wide‐spectrum synthetic applications. This review supplies an encyclopedic document regarding the approaches developed for the synthesis of fused‐cyclic quinolines based on ring volume size reported thus far. This collected information will be valuable for medicinal chemists to obtain knowledge regarding designing new approaches in order to access biological active compounds.

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“…Moreover, the Ugi‐4CR has influenced a growing body of research in material sciences and chemical biology [34,35] . Recent developments exemplify the versatility of the Ugi‐adduct, describing the preparation high utility scaffolds via metal‐mediated or metal‐free post‐Ugi transformations [36–43] . In addition to the Ugi reaction, a battery of MCRs are available in the tool box of the modern day chemist namely Petasis, Povarov and Groebke‐Blackburn‐Bienaymé reactions to name but a few [44–46] .…”

Section: Mcr: a Brief Historymentioning

confidence: 99%

Six‐Component Reactions and Beyond: The Nuts and Bolts

Hooshmand

Yazdani²,

Hulme

2022

Eur J Org Chem

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The deployment of multicomponent reactions (MCRs), defined as containing three or more reactants, not only enjoys pot, atom, and step‐economy in the synthesis of novel complex molecules but also aligns with sustainable chemistry principles as a green symphony. Generally, more components lead to more complexity, and are taken to an extreme ‘‘higher‐order’’ MCRs, where six or even more components react in a one‐pot, have been developed, although they remain scarce compared to their 3, 4 and 5‐component relatives. On this topic, the rich footprint of isocyanides in MCRs has been fruitful in delivering higher order six to eight‐component reactions through mechanistically similar pathways. The present review encompasses a brief history of MCRs and their product utility, followed by a thorough discussion of the principles of reaction design that enabled the discovery of higher‐order MCRs, spanning 6 to 8‐components. Future challenges and opportunities will also be elaborated.

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Highly Substituted Medium-Sized Ring-Fused Azocinoquinoline Scaffolds by Post-Ugi-4CR Reductive Carbopalladation Cyclization

Cited by 18 publications

References 40 publications

Recent Advances in the Synthesis of Peptidomimetics via Ugi Reactions

Recent Advances in the Synthesis of Peptidomimetics via Ugi Reactions

Recent Advances in the Synthesis of Fused‐Cyclic Quinolines

Six‐Component Reactions and Beyond: The Nuts and Bolts

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