Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex

Das, Kalicharan; Mondal, Avijit; Pal, Debjyoti; Srimani, Dipankar

doi:10.1021/acs.orglett.9b00939

Cited by 98 publications

(48 citation statements)

References 62 publications

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“…Synthesis of 3‐phenylquinolin‐2‐amine (5) . To a round‐bottomed flask filled with 4‐phenyltetrazolo[1,5‐ a ]quinoline ( 4a ) (123 mg, 0.5 mmol) was diluted with DMF (2 mL).…”

Section: Methodsmentioning

confidence: 99%

Azide‐Triggered Bicyclization of o‐Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5‐a]quinolines

et al. 2019

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An efficient and rapid synthetic approach for the synthesis of tetrazolo[1,5‐a]quinolines has been developed employing the reaction of o‐alkynylisocyanobenzenes with sodium azide. The present strategy involved nucleophilic addition of azide to isocyanide followed by 6‐endo cyclization. The reaction gives access to a collection of tetrazolo[1,5‐a]quinolines with broad functional group in moderate to high yields under metal‐, and base‐free conditions.

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“…Synthesis of 3‐phenylquinolin‐2‐amine (5) . To a round‐bottomed flask filled with 4‐phenyltetrazolo[1,5‐ a ]quinoline ( 4a ) (123 mg, 0.5 mmol) was diluted with DMF (2 mL).…”

Section: Methodsmentioning

confidence: 99%

Azide‐Triggered Bicyclization of o‐Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5‐a]quinolines

et al. 2019

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“…The phosphine free manganese complex Mn‐4 developed by the Srimani group was also utilized for the synthesis of aminoquinolines via the sequential ADC and N ‐alkylation of 2‐aminobenzyl alcohol 25 and nitrile 10 (Scheme ) . The method was extended for the synthesis of quinazoline derivatives by using benzonitriles 10’ as the coupling partner with 25 .…”

Section: C−c/c−x/x−x Multiple Bond Formationsmentioning

confidence: 99%

Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions

Waiba

Maji

2020

ChemCatChem

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Acceptorless dehydrogenative coupling (ADC) has emerged as a powerful tool in the chemists’ arsenal for the construction of various carbon‐carbon and carbon‐heteroatom bonds. These protocols are highly atom economical and environmentally benign as they do not require pre‐functionalized starting material and produce only dihydrogen (and water) as the by‐product. This technique, coupled with Earths’ abundant and less toxic manganese catalysis, can prove to be a vital strategy for the generation of molecular complexity from simple starting materials. Manganese catalyzed DHC has been of growing interest, and various low‐ and high‐valent manganese catalysts have been developed. These catalysts were demonstrated to show excellent catalytic activity for the formation of carbon‐carbon, carbon‐heteroatom bonds, and cascade reactions. In this mini‐review, we would like to highlight the recent progress that has been made in manganese catalyzed ADC reactions.

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“…Very recently Srimani et al. demonstrated a sustainable approach for the synthesis of 2‐aminoquinolines and quinazolines by sensible application of the manganese‐catalysed acceptor‐less dehydrogenative annulation of nitriles with 2‐aminobenzyl alcohols (Scheme ) . Under the optimised reaction conditions, the previously mentioned manganese‐NNS pincer catalytic system 123 was used at a 5 mol% loading in xylene at 140 °C.…”

Section: Synthesis and Derivatisation Of Heterocyclic Compoundsmentioning

confidence: 99%

“… Proposed mechanism for the Mn‐catalysed synthesis of quinolones and quinoxalines by Srimani et al. (reproduced with permission from Ref …”

Section: Synthesis and Derivatisation Of Heterocyclic Compoundsmentioning

confidence: 99%

Manganese‐Catalysed Dehydrogenative Coupling – An Overview

et al. 2020

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Manganese‐catalysed reactions have attracted great attention recently due to the high relative abundance and cheap and eco‐friendly behaviour. Applications of manganese catalysis in cross‐dehydrogenative coupling are among the hottest areas since 90% of the contributions are very recent. Dehydrogenation of alcohols using Mn‐pincer systems is highly explored nowadays for cross‐coupling to synthesise a variety of products and Mn‐catalysed C−H activation, and radical reactions are applied in dehydrogenative couplings of various synthons. This review focuses on the synthesis of synthetically as well as biologically important motifs such as carbonyl compounds, olefins, nitrogen heterocycles, amines, imines, etc. using manganese‐catalysed dehydrogenative cross‐coupling reactions.

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Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex

Cited by 98 publications

References 62 publications

Azide‐Triggered Bicyclization of o‐Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5‐a]quinolines

Azide‐Triggered Bicyclization of o‐Alkynylisocyanobenzenes: Synthesis of Tetrazolo[1,5‐a]quinolines

Manganese Catalyzed Acceptorless Dehydrogenative Coupling Reactions

Manganese‐Catalysed Dehydrogenative Coupling – An Overview

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