[DDQM][HSO4]/TBHP as a multifunctional catalyst for the metal free tandem oxidative synthesis of 2-Phenylquinazolin-4(3H)-ones

Bidyutjyoti Dutta; Nilakshi Dutta; Apurba Dutta; Montu Gogoi; Sanjay Mehra; Arvind Kumar; Kalyanjyoti Deori; Diganta Sarma

doi:10.1021/acs.joc.2c00908

[DDQM][HSO4]/TBHP as a multifunctional catalyst for the metal free tandem oxidative synthesis of 2-Phenylquinazolin-4(3H)-ones

Bidyutjyoti Dutta, Nilakshi Dutta, Apurba Dutta, Montu Gogoi, Sanjay Mehra, Arvind Kumar, Kalyanjyoti Deori^*, Diganta Sarma

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

18 Citations (Scopus)

Abstract

A bifunctional ionic liquid (IL) [DDQM][HSO4] has been designed and explored as a three-way catalyst for the synthesis of 2-phenylquinazolin-4(3H)-ones from anthranilamide and benzyl alcohol in 3.5 min incorporating microwave irradiation. Photochemically the reaction proceeds for 4 h at room temperature and thermally for 8 h at 120 °C. Further IL-assisted metal, solvent, and base free in situ oxidation of benzyl alcohols to aldehydes shows its task specificity. The multifunctionality of the IL was reestablished with the synthesis of two Wnt pathway antagonists.

Original language	English
Pages (from-to)	14748–14752
Journal	Journal of Organic Chemistry
Volume	88
Issue number	20
Early online date	12 Aug 2023
DOIs	https://doi.org/10.1021/acs.joc.2c00908
Publication status	Published - 20 Oct 2023
Externally published	Yes

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title = "[DDQM][HSO4]/TBHP as a multifunctional catalyst for the metal free tandem oxidative synthesis of 2-Phenylquinazolin-4(3H)-ones",

abstract = "A bifunctional ionic liquid (IL) [DDQM][HSO4] has been designed and explored as a three-way catalyst for the synthesis of 2-phenylquinazolin-4(3H)-ones from anthranilamide and benzyl alcohol in 3.5 min incorporating microwave irradiation. Photochemically the reaction proceeds for 4 h at room temperature and thermally for 8 h at 120 °C. Further IL-assisted metal, solvent, and base free in situ oxidation of benzyl alcohols to aldehydes shows its task specificity. The multifunctionality of the IL was reestablished with the synthesis of two Wnt pathway antagonists.",

author = "Bidyutjyoti Dutta and Nilakshi Dutta and Apurba Dutta and Montu Gogoi and Sanjay Mehra and Arvind Kumar and Kalyanjyoti Deori and Diganta Sarma",

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doi = "10.1021/acs.joc.2c00908",

language = "English",

volume = "88",

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journal = "Journal of Organic Chemistry",

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T1 - [DDQM][HSO4]/TBHP as a multifunctional catalyst for the metal free tandem oxidative synthesis of 2-Phenylquinazolin-4(3H)-ones

AU - Dutta, Bidyutjyoti

AU - Dutta, Nilakshi

AU - Dutta, Apurba

AU - Gogoi, Montu

AU - Mehra, Sanjay

AU - Kumar, Arvind

AU - Deori, Kalyanjyoti

AU - Sarma, Diganta

PY - 2023/10/20

Y1 - 2023/10/20

N2 - A bifunctional ionic liquid (IL) [DDQM][HSO4] has been designed and explored as a three-way catalyst for the synthesis of 2-phenylquinazolin-4(3H)-ones from anthranilamide and benzyl alcohol in 3.5 min incorporating microwave irradiation. Photochemically the reaction proceeds for 4 h at room temperature and thermally for 8 h at 120 °C. Further IL-assisted metal, solvent, and base free in situ oxidation of benzyl alcohols to aldehydes shows its task specificity. The multifunctionality of the IL was reestablished with the synthesis of two Wnt pathway antagonists.

AB - A bifunctional ionic liquid (IL) [DDQM][HSO4] has been designed and explored as a three-way catalyst for the synthesis of 2-phenylquinazolin-4(3H)-ones from anthranilamide and benzyl alcohol in 3.5 min incorporating microwave irradiation. Photochemically the reaction proceeds for 4 h at room temperature and thermally for 8 h at 120 °C. Further IL-assisted metal, solvent, and base free in situ oxidation of benzyl alcohols to aldehydes shows its task specificity. The multifunctionality of the IL was reestablished with the synthesis of two Wnt pathway antagonists.

U2 - 10.1021/acs.joc.2c00908

DO - 10.1021/acs.joc.2c00908

M3 - Article

SN - 0022-3263

VL - 88

SP - 14748

EP - 14752

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 20

ER -

[DDQM][HSO4]/TBHP as a multifunctional catalyst for the metal free tandem oxidative synthesis of 2-Phenylquinazolin-4(3H)-ones

Abstract

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