(3 + 2) cycloaddition of 2-alkoxynaphthalenes with azaoxyallyl cations: access to benzo[<i>e</i>]indolones

Biswas, S.; Duari, Surajit; Maity, Srabani; Roy, Arnab; Elsharif, Asma M.; Biswas, Srijit

doi:10.1039/d2ob01441f

Cited by 8 publications

(1 citation statement)

References 42 publications

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“…After an initial screening, the reaction temperature and time were fixed at 120 °C and 14 h, respectively. As a continuation of our research efforts to develop transition metal-free reactions, a variety of Brønsted acids such as MeOTf, p -TSA·H 2 O, H 3 PO 3 , etc., were tested and the desired product 3a was generated in low yields (Table , entries 1–6). Through various trials, TfOH (20 mol %) in toluene at 120 °C provided the best result to furnish the desired benzofuran 3a in an 84% yield.…”

Section: Resultsmentioning

confidence: 99%

Regioselective Transition Metal-Free Catalytic Ring Opening of 2H-Azirines by Phenols and Naphthols; One-Pot Access to Benzo- and Naphthofurans

Roy,

Biswas,

Duari

et al. 2023

J. Org. Chem.

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Benzofuran and naphthofuran derivatives are synthesized from readily available phenols and naphthols. Regioselective ring openings of 2H-azirine followed by in situ aromatization using a catalytic amount of Brønsted acid have established the novelty of the methodology. The involvement of a series of 2H-azirines with a variety of phenols, 1-naphthols, and 2-naphthols showed the generality of the protocol. In-depth density functional theory calculations revealed the reaction mechanism with the energies of the intermediates and transition states of a model reaction. An alternate pathway of the mechanism has also been proposed with computer modeling.

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Section: Resultsmentioning

confidence: 99%

Regioselective Transition Metal-Free Catalytic Ring Opening of 2H-Azirines by Phenols and Naphthols; One-Pot Access to Benzo- and Naphthofurans

Roy,

Biswas,

Duari

et al. 2023

J. Org. Chem.

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Synthesis of tetracyclic 4H‐benzo[5,6]chromeno[3,4‐d]oxazoles via palladium‐catalyzed intramolecular direct heteroarylation

Kumar

Kajol

Nayak

et al. 2023

Chemistry An Asian Journal

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We report a palladium-catalyzed intramolecular direct heteroarylation of oxazole tethered β-naphthols to access corresponding tetracyclic 4H-benzo [5,6]chromeno [3,4d]oxazoles. Various functional groups are well tolerated and furnished the desired products in good to excellent yields under the present reaction conditions. The scale-up reaction and synthetic utility of the resulting molecules have been demonstrated. Moreover, UV/vis absorption and fluorescence emission properties have been evaluated for these polyheterocyclic compounds.

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α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

Nishikata

2024

ChemistryOpen

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This review introduces the synthetic organic chemical value of α‐bromocarbonyl compounds with tertiary carbons. This α‐bromocarbonyl compound with a tertiary carbon has been used primarily only as a radical initiator in atom transfer radical polymerization (ATRP) reactions. However, with the recent development of photo‐radical reactions (around 2010), research on the use of α‐bromocarbonyl compounds as tertiary alkyl radical precursors became popular (around 2012). As more examples were reported, α‐bromocarbonyl compounds were studied not only as radicals but also for their applications in organometallic and ionic reactions. That is, α‐bromocarbonyl compounds act as nucleophiles as well as electrophiles. The carbonyl group of α‐bromocarbonyl compounds is also attractive because it allows the skeleton to be converted after the reaction, and it is being applied to total synthesis. In our survey until 2022, α‐bromocarbonyl compounds can be used to perform a full range of reactions necessary for organic synthesis, including multi‐component reactions, cross‐coupling, substitution, cyclization, rearrangement, stereospecific reactions, asymmetric reactions. α‐Bromocarbonyl compounds have created a new trend in tertiary alkylation, which until then had limited reaction patterns in organic synthesis. This review focuses on how α‐bromocarbonyl compounds can be used in synthetic organic chemistry.

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(3 + 2) cycloaddition of 2-alkoxynaphthalenes with azaoxyallyl cations: access to benzo[e]indolones

Abstract: A reaction between 2-alkoxynaphthalene and in situ formed azaoxyallyl cation has been reported under ambient reaction condition. (3+2) cycloaddition reaction followed by aryl C–OMe/C–OEt bond cleavage produces a variety of...

Cited by 8 publications

References 42 publications

Regioselective Transition Metal-Free Catalytic Ring Opening of 2H-Azirines by Phenols and Naphthols; One-Pot Access to Benzo- and Naphthofurans

Regioselective Transition Metal-Free Catalytic Ring Opening of 2H-Azirines by Phenols and Naphthols; One-Pot Access to Benzo- and Naphthofurans

Synthesis of tetracyclic 4H‐benzo[5,6]chromeno[3,4‐d]oxazoles via palladium‐catalyzed intramolecular direct heteroarylation

α‐Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source

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