Tropylium-BF4 as Organocatalyst for Microwave-assisted Beckmann rearrangement in [TMG][BF4]: One-pot conversion of Ketones to Amides

被引：10

作者：

Anchi, Athmanand ^{[1
]}

Kalkhambkar, Rajesh G. ^{[1
]}

Sutar, Suraj M. ^{[2
]}

Naik, Ravi S. ^{[3
]}

Refat, Moamen S. ^{[4
]}

Adam, Abdel Majid A. ^{[4
]}

Mohammed Alsuhaibani, Amnah ^{[5
]}

机构：

[1] Karnatak Univ Karnatak Sci Coll, Dept Chem, Dharwad 580001, Karnataka, India

[2] Yashwantrao Chavan Mahavidyalaya, Dept Chem, Halkarni 416552, Maharashtra, India

[3] Mahantswami Arts Sci & Commerce Coll Coll, Dept Chem, Haunsbhavi 581109, Karnataka, India

[4] Taif Univ, Coll Sci, Dept Chem, Taif 21944, Saudi Arabia

[5] Princess Nourah bint Abdulrahman Univ, Coll Educ, Dept Phys Sport Sci, Riyadh 11671, Saudi Arabia

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 23期

关键词：

Beckmann rearrangement; Ionic liquids; Ketones to Amides; Microwave-irradiation; Tropylium-BF4; HIGHLY EFFICIENT SYNTHESIS; IONIC LIQUID; DIVERSE LIBRARIES; IMIDAZOLIUM-ILS; FACILE ACCESS; AMINES; ACID; ACETYLATION; CAPROLACTAM; ACYLATION;

D O I：

10.1002/slct.202301431

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The microwave assisted one pot efficient conversion of ketones into respective amides has been achieved by utilization of environmentally benign catalytic system tailored by tropylium tetrafluoroborate (Tp(+)BF(4)(-)) and 1,1,3,3-tetramethylguanidinium tetrafluoroborate [TMG][BF4]. The mild reaction conditions, shorter reaction time, and affordable catalytic system are the key points that highlight the importance. The high product yield and ease of recycling impacts the successful product conversion.

引用

页数：12

共 62 条

[1] Aryltriazenes as Coupling Partners in the Hiyama, Hiyama-Suzuki and Hiyama-Heck Cross-Coupling Reactions Using Conventional and Ionic Liquid Reagents and Solvents [J].

Anchi, Athmanand ;

Malunavar, Shruti S. S. ;

Naik, Ravi S. S. ;

Kalkhambkar, Rajesh G. G. ;

Laali, Kenneth K. K. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (45)

[2] Tropylium-BF4 as Organocatalyst for Efficient Synthesis of Nitriles from Aldoximes; Synthetic Scope and Mechanistic Insights [J].

Anchi, Athmanand ;

Sutar, Suraj M. ;

Kalkhambkar, Rajesh G. ;

Borosky, Gabriela L. ;

Laali, Kenneth K. .

CHEMISTRYSELECT, 2022, 7 (35)

[3] One-pot oximation-Beckmann rearrangement of ketones and aldehydes to amides of industrial interest: Acetanilide, caprolactam and acetaminophen [J].

Arico, Fabio ;

Quartarone, Giuseppe ;

Rancan, Elia ;

Ronchin, Lucio ;

Tundo, Pietro ;

Vavasori, Andrea .

CATALYSIS COMMUNICATIONS, 2014, 49 :47-51

[4] Rhodium-catalyzed Beckmann rearrangement [J].

Arisawa, M ;

Yamaguchi, M .

ORGANIC LETTERS, 2001, 3 (02) :311-312

[5] The Beckmann rearrangement [J].

Blatt, AH .

CHEMICAL REVIEWS, 1933, 12 (02) :215-260

[6] Ketones to amides via a formal Beckmann rearrangement in 'one pot': a solvent-free reaction promoted by anhydrous oxalic acid. Possible analogy with the Schmidt reaction [J].

Chandrasekhar, S ;

Gopalaiah, K .

TETRAHEDRON LETTERS, 2003, 44 (40) :7437-7439

[7] β-peptides:: From structure to function [J].

Cheng, RP ;

Gellman, SH ;

DeGrado, WF .

CHEMICAL REVIEWS, 2001, 101 (10) :3219-3232

[8]

Das B, 2000, J CHEM RES, P482

[9] An easy method for the generation of amides from ketones by a Beckmann type rearrangement mediated by microwave [J].

Eshghi, H ;

Gordi, Z .

SYNTHETIC COMMUNICATIONS, 2003, 33 (17) :2971-2978

[10] P2O5/SiO2-catalyzed one-pot synthesis of amides from ketones via Schmidt reaction under microwave irradiation in dry media [J].

Eshghi, Hossein ;

Hassankhani, Asadollah .

SYNTHETIC COMMUNICATIONS, 2006, 36 (15) :2211-2216

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