Synthesis of Highly Functionalized Tricyclic Chromenopyrazole Frameworks <i>via</i> Intramolecular Azomethine Imine 1,3‐Dipolar Cycloaddition (IAIDC)

Bakthadoss, Manickam; Agarwal, V. K.

doi:10.1002/slct.201801269

Cited by 13 publications

(3 citation statements)

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“…Similarly, Bakthadoss and Agarwal reported the synthesis of angularly substituted tricyclic chromenopyrazoles ( 161 ). The reaction cascade proceeded through intramolecular 1,3‐dipolar cycloaddition of azomethine imine generated from o ‐allylated salicylaldehydes ( 159 ) and aryl hydrazines ( 160 ) . This protocol included the diastereoselective creation of two rings and two contiguous stereocenters (Scheme ).…”

Section: Divergent Synthesis Of Various Polycyclic Compoundsmentioning

confidence: 99%

“…The reaction cascade proceeded through intramolecular 1,3-dipolar cycloaddition of azomethine imine generated from o-allylated salicylaldehydes (159)a nd aryl hydrazines( 160). [64] This protocol included the diastereoselective creation of two rings and two contiguous stereocenters (Scheme 38). The high diastereoselectivity and stereospecificity are attributed to the anti orientation of the aryl group with respect to the olefinicg eometry of the adjacent ester moiety owing to the initial olefinic geometry found in the starting materials.…”

Section: Synthesis Of Benzopyran-annulatedsystemsmentioning

confidence: 99%

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Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp³ Content and Privileged Architectures

Sebastian

Srinivasulu

Abu‐Yousef

et al. 2019

Chemistry A European J

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Diversity‐oriented synthesis (DOS) has become a powerful synthetic tool that facilitates the construction of nature‐inspired and privileged chemical space, particularly for sp3‐rich non‐flat scaffolds, which are needed for phenotypic screening campaigns. These diverse compound collections led to the discovery of novel chemotypes that can modulate the protein function in underrepresented biological space. In this context, starting material‐driven DOS is one of the most important tools used to build diverse compound libraries with rich stereochemical and scaffold diversity. To this end, ene/yne tethered salicylaldehyde derivatives have emerged as a pluripotent chemical platform, the products of which led to the construction of a privileged chemical space with significant biological activities. In this review, various domino transformations employing o‐alkene/alkyne tethered aryl aldehyde/ketone platforms are described and discussed, with emphasis on the period from 2011 to date.

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Section: Divergent Synthesis Of Various Polycyclic Compoundsmentioning

confidence: 99%

Section: Synthesis Of Benzopyran-annulatedsystemsmentioning

confidence: 99%

Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp³ Content and Privileged Architectures

Sebastian

Srinivasulu

Abu‐Yousef

et al. 2019

Chemistry A European J

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“…This diazo compound has been used for various organic transformations such as alkylation, carbene generation, nucleophilic addition, homologation, ring expansions, etc . Ylide-based cycloaddition reactions is considered as one of the powerful synthetic strategies for the rapid formation of complex molecules from readily available substrates. Among the various ylide-based cycloadditions, the 1,3-dipolar cycloaddition of carbonyl ylide is studied extensively and used for the synthesis of many natural products and biologically useful molecules .…”

Section: Introductionmentioning

confidence: 99%

Rhodium-Catalyzed Diastereoselective [3 + 2] Cycloaddition of Carbonyl Ylide: An Access to the Core Ring System of Cordigol and Lophirone H

Bakthadoss

Agarwal

2020

J. Org. Chem.

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This paper describes a new synthetic strategy for the construction of tricyclic chromeno/quinolino furan frameworks via creation of two new rings and three contiguous stereogenic centers with high diastereoselectivity through a rhodium-catalyzed intramolecular carbonyl ylide cycloaddition reaction for the first time. This protocol allows the synthesis of the core ring system of natural products such as cordigol and lophirone H.

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[3 + 2] Cycloadditions of Azomethine Imines

Grošelj

Svete

2020

Organic Reactions

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In spite of their late discovery in the middle of 20 th century, the importance of azomethine imines and their [3+2] cycloaddition reactions has grown constantly throughout the decades. Today, [3+2] cycloadditions of azomethine imines have become indispensable in the preparation of pyrazole derivatives with all degrees of saturation. The structural diversity of azomethine imines is wide and comprises acyclic, C , N ‐cyclic, N , N ‐cyclic, and C , N , N ‐cyclic 1,3‐dipoles. Although electron‐deficient dipolarophiles are preferred, electron‐rich dipolarophiles, such as enol ethers and enamines, are also commonly used in these reactions. Compared to cyclocondensation methods and [3+2] cycloadditions with diazoalkanes and nitrile imines, [3+2] cycloadditions with azomethine imines provide access to a greater diversity of pyrazole derivatives with all degrees of saturation. As with other 1,3‐dipolar cycloadditions, a concerted and nearly synchronous mechanism has been proposed for most [3+2] cycloadditions of azomethine imines, although a stepwise mechanism may be viable in some cases. Several examples of asymmetric [3+2] cycloadditions of azomethine imines that afford non‐racemic cycloadducts with high enantioselectivity have been reported. These asymmetric cycloadditions are performed with various types of transition metal catalysts and organocatalysts, and indicate their potential for the asymmetric synthesis of saturated pyrazole derivatives. Finally, many examples of copper‐catalyzed and thermal, strain‐promoted [3+2] cycloadditions of azomethine imines (in particular sydnones) clearly indicate wide applicability of these reactions in bioconjugation, fluorescent labelling, materials functionalization, and other applications outside the realm of pure organic synthesis.

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Synthesis of Highly Functionalized Tricyclic Chromenopyrazole Frameworks via Intramolecular Azomethine Imine 1,3‐Dipolar Cycloaddition (IAIDC)

Cited by 13 publications

References 51 publications

Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp³ Content and Privileged Architectures

Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp³ Content and Privileged Architectures

Rhodium-Catalyzed Diastereoselective [3 + 2] Cycloaddition of Carbonyl Ylide: An Access to the Core Ring System of Cordigol and Lophirone H

[3 + 2] Cycloadditions of Azomethine Imines

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Synthesis of Highly Functionalized Tricyclic Chromenopyrazole Frameworks via Intramolecular Azomethine Imine 1,3‐Dipolar Cycloaddition (IAIDC)

Cited by 13 publications

References 51 publications

Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp3 Content and Privileged Architectures

Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp3 Content and Privileged Architectures

Rhodium-Catalyzed Diastereoselective [3 + 2] Cycloaddition of Carbonyl Ylide: An Access to the Core Ring System of Cordigol and Lophirone H

[3 + 2] Cycloadditions of Azomethine Imines

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Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp³ Content and Privileged Architectures

Domino Transformations of Ene/Yne Tethered Salicylaldehyde Derivatives: Pluripotent Platforms for the Construction of High sp³ Content and Privileged Architectures