Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)

Varga, Valentina; Ábrányi‐Balogh, Péter; Milen, Mátyás

doi:10.3390/chemistry2020037

“…The same reaction is applicable to the synthesis of 1-carbamatoalkyl-2-naphthols when carbamates are used as reaction partners [48][49][50][51][52][53]. However, the reports on the synthesis of 1carbamatoalkyl-2-naphthols over the last 3 years are limited [54,55]. The generally accepted reaction mechanism of the acid-promoted three-component Mannich condensation of 2naphthol with aldehydes and amides proceeds with the initial formation of highly reactive ortho-quinone methides.…”

Section: Synthesis Of Amidoalkyl Naphthols Via Multicomponent Mannich...mentioning

confidence: 99%

Amidoalkyl Naphthols as Important Bioactive Substances and Building Blocks: A Review on the Current Catalytic Mannich-Type Synthetic Approaches

Petkov

¹

,

Simeonov

²

2023

Applied Sciences

2

0

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Currently, 1-amidoalkyl-2-naphthol derivatives are of increasing interest due to their biological activities and further use in the preparation of other important bioactive molecules, such as aminoalkyl naphthols and oxazines. The synthesis of 1-amidoalkyl-2-naphthol moiety is usually achieved by employing one-pot multicomponent Mannich reactions. This review covers the recent reports on 1-amidoalkyl-2-naphthols’ preparation with the use of different catalysts and summarizes the available published data for the period of the last 3 years. It also puts emphasis on the structure, synthetic transformation and biological importance of this class of products.

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Advanced Catalytic Syntheses of 1,3-Oxazine Derivatives via Electrophilic Substitution Using Mono- and Bimetallic Phosphate Catalysts: Co₃(PO 4 ) 2 and CoCa 3 (HPO 4 )(PO 4 ) 2 (OH)

hallaoui,

FERRAA,

MERROUN

et al. 2024

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This research introduces a novel catalytic approach for the synthesis of 1,3-oxazinone derivatives through a multicomponent reaction that relies on an electrophilic substitution mechanism, employing two cobalt-based phosphate catalysts. This approach, allowed us to synthesize oxazine derivatives, known for their significant biological activities, achieving impressive yields of up to 97% in a remarkably short time of only 7 minutes, all under conditions environmentally friendly according to the principles of green chemistry using the ethanol/water mixture as a green solvent. In our study, we utilized two catalysts derived from cobalt-modified phosphate, which were synthesized in our laboratory using simple methods. The first support consists of a monometallic catalyst, denoted as Co3(PO4)2, whereas the second is a bimetallic phosphate catalyst modified with cobalt and calcium CoCa3(HPO4)(PO4)2(OH). Our developed methods had various advantages including simplicity of the process, rapid reaction time, simple clean-up, ability to recover and reuse the catalyst and overall simplicity. All these advantages render this developed approach effective and viable for synthesizing oxazine derivatives suitable for large-scale applications.

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Advanced Catalytic Approaches for Synthesizing 1,2-dihydro-1-aryl-3H-naphtho[1,2-e]-[1,3]oxazin-3-one Derivatives through Electrophilic Substitution Reactions using Mono- and Bimetallic Phosphate Catalysts: A Study of Co₃(PO₄)₂ and CoCa₃(HPO₄)(PO₄)₂(OH)

HALLAOUI,

FERRAA,

MERROUN

et al. 2024

Preprint

0

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This research introduces a novel catalytic approach for the synthesis of 1,3-oxazinone derivatives through a multicomponent reaction that relies on an electrophilic substitution mechanism, employing two cobalt-based phosphate catalysts. This approach, allowed us to synthesize oxazine derivatives, known for their significant biological activities, achieving impressive yields of up to 97% in a remarkably short time of only 7 minutes, all under conditions environmentally friendly according to the principles of green chemistry using the ethanol/water mixture as a green solvent. In our study, we utilized two catalysts derived from cobalt-modified phosphate, which were synthesized in our laboratory using simple methods. The first support consists of a monometallic catalyst, denoted as Co3(PO4)2, whereas the second is a bimetallic phosphate catalyst modified with cobalt and calcium CoCa3(HPO4)(PO4)2(OH). Our developed methods had various advantages including simplicity of the process, rapid reaction time, simple clean-up, ability to recover and reuse the catalyst and overall simplicity. All these advantages render this developed approach effective and viable for synthesizing oxazine derivatives suitable for large-scale applications.

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Synthesis of Naphthoxazinones in a One-Pot Two-Step Manner by the Application of Propylphosphonic Anhydride (T3P®)

Cited by 3 publications

References 36 publications

Amidoalkyl Naphthols as Important Bioactive Substances and Building Blocks: A Review on the Current Catalytic Mannich-Type Synthetic Approaches

Amidoalkyl Naphthols as Important Bioactive Substances and Building Blocks: A Review on the Current Catalytic Mannich-Type Synthetic Approaches

Advanced Catalytic Syntheses of 1,3-Oxazine Derivatives via Electrophilic Substitution Using Mono- and Bimetallic Phosphate Catalysts: Co₃(PO 4 ) 2 and CoCa 3 (HPO 4 )(PO 4 ) 2 (OH)

Advanced Catalytic Approaches for Synthesizing 1,2-dihydro-1-aryl-3H-naphtho[1,2-e]-[1,3]oxazin-3-one Derivatives through Electrophilic Substitution Reactions using Mono- and Bimetallic Phosphate Catalysts: A Study of Co₃(PO₄)₂ and CoCa₃(HPO₄)(PO₄)₂(OH)

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