Advances in transition metal-catalyzed C–H amination strategies using anthranils

Aher, Yogesh N.; Bhaduri, Nilanjan; Pawar, Amit B.

doi:10.1039/d3ob01421e

Cited by 8 publications

(1 citation statement)

References 75 publications

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“…2 The unique reactivity of p -QMs, driven by rearomatization, has enabled them to undergo a variety of nucleophilic additions under a plethora of reaction conditions. Despite the tremendous progress made with regard to the utilization of p -QMs as Michael acceptors for the creation of C–C, 3 C–S, 4 C–P, 5 C–B, 6 and C–Si 7 bonds, examples of the addition of N-heterocycle-based N-centered nucleophiles, especially those involving amides/imides, are limited (Scheme 1a ). 8…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Base-Promoted 1,6-Aza-Michael Addition of Azauracils to para-Quinone Methides

2023

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Here, we report an efficient higher order conjugate addition of azauracils to substituted para-Quinone methides (p-QMs) mediated by triethylamine to furnish hitherto unknown diarylmethane scaffolds through construction of a C-N bond. The protocol features mild conditions, high atom economy, and broad scope, and enables convenient access to biologically relevant new chemical entities (NCEs) comprising p-QM and azauracil hybrid in good to excellent yields.

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Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Base-Promoted 1,6-Aza-Michael Addition of Azauracils to para-Quinone Methides

2023

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Benzoisoxazoles as Privileged Scaffolds in the Design and Synthesis of N‐containing Molecules: A Recent Update

Chen,

Ma,

Kang

et al. 2024

Eur J Org Chem

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Benzoisoxazoles, with a distinctive 10‐π‐electron system and significant polarity, readily trigger N‐O bond cleavage, enabling multifaceted applications in organic synthesis. Over the past decade, the exponentially increased use of benzoisoxazoles towards the synthesis of highly valuable N‐containing scaffolds, especially N‐heterocycles, has garnered substantial attention. In this review, we summarize recent developments in the transformation of 2,1‐ and 1,2‐benzoisoxazoles since 2015, highlighting the neglected resemblances of these two nitroxy heterocycles. Key processes in the assorted reactions of benzoisoxazoles, including mechanisms, scope, catalyst‐controlled chemodivergence, current limitations, and developmental prospects, are also introduced and discussed.

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Skeletal Editing via Transition‐Metal‐Catalyzed Nitrene Insertion

Bhatti,

Gupta,

Chaudhari

et al. 2024

The Chemical Record

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Metal‐nitrenes are valuable reactive intermediates for synthesis and are widely used to construct biologically relevant scaffolds, complexes and functionalized molecules. The ring expansion of cyclic molecules via single‐nitrogen‐atom insertion via nitrene or metal‐nitrenoid intermediates has emerged as a promising modern strategy for driving advantageous nitrogen‐rich compound synthesis. In recent years, the catalytic insertion of a single nitrogen atom into carbocycles, leading to N‐heterocycles, has become an important focus of modern synthetic approaches with applications in medicinal chemistry, materials science, and industry. Catalytic single‐nitrogen‐atom insertions have been increasing in prominence in modern organic synthesis due to their capability to construct high‐value added nitrogen‐containing heterocycles from simple feedstocks. In this review, we will discuss the rapidly growing field of skeletal editing via single‐nitrogen‐atom insertion using transition metal catalysis to access nitrogen‐containing heterocycles, with a focus on nitrogen insertion across a wide spectrum of carbocycles.

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Advances in transition metal-catalyzed C–H amination strategies using anthranils

Abstract: Modern times have witnessed an uprise in the synthesis and derivatization of nitrogen-containing fused heterocycles. Amination reactions involving nitrene chemistry have always been the most convenient choice for the incorporation...

Cited by 8 publications

References 75 publications

Base-Promoted 1,6-Aza-Michael Addition of Azauracils to para-Quinone Methides

Base-Promoted 1,6-Aza-Michael Addition of Azauracils to para-Quinone Methides

Benzoisoxazoles as Privileged Scaffolds in the Design and Synthesis of N‐containing Molecules: A Recent Update

Skeletal Editing via Transition‐Metal‐Catalyzed Nitrene Insertion

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