A facile synthesis of 1-aryl pyrroles by Clauson-Kaas reaction using oxone as a  Catalyst under microwave irradiation

Gullapelli, Kumaraswamy; Brahmeshwari, G.; Ravichander, M.

doi:10.4314/bcse.v33i1.14

Cited by 11 publications

(2 citation statements)

References 25 publications

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“…Gullapelli et al [ 92 ] described the Clauson–Kaas synthesis of N -arylpyrroles 79 under microwave irradiation using oxone (2KHSO 5 ∙KHSO 4 ∙K 2 SO 4 ) as a catalyst ( Scheme 38a ). Many solvents (EtOH, CH 3 CN, THF, DMF, H 2 O, neat), reaction times (10–22 minutes), and amount of oxone were investigated in order to stabilize the best reaction conditions.…”

Section: Reviewmentioning

confidence: 99%

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

Singh¹,

Kumar²

2023

Beilstein J. Org. Chem.

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Pyrrole is an important aromatic heterocyclic scaffold found in many natural products and predominantly used in pharmaceuticals. Continuous efforts are being made to design and synthesize various pyrrole derivatives using different synthetic procedures. Among them, the Clauson–Kaas reaction is a very old and well-known method for synthesizing a large number of N-substituted pyrroles. In recent years, due to global warming and environmental concern, research laboratories and pharmaceutical industries around the world are searching for more environmentally friendly reaction conditions for synthesizing compounds. As a result, this review describes the use of various eco-friendly greener protocols to synthesize N-substituted pyrroles. This synthesis involves the reaction of various aliphatic/aromatic primary amines, and sulfonyl primary amines with 2,5-dimethoxytetrahydrofuran in the presence of numerous acid catalysts and transition metal catalysts. The goal of this review is to summarize the synthesis of various N-substituted pyrrole derivatives using a modified Clauson–Kaas reaction under diverse conventional and greener reaction conditions.

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Section: Reviewmentioning

confidence: 99%

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

Singh¹,

Kumar²

2023

Beilstein J. Org. Chem.

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“…On the other hand, quite recently, Ravichander's group revealed a new and facile synthesis of N ‐substituted pyrrole derivatives 628 a – c by means of Clauson‐Kaas reaction involving 2,5‐dimethoxytetrahydrofuran 627 with a variety of arylamines in the presence of oxone under microwave irradiation (Scheme 194). [457] The plausible mechanism for oxone supported synthesis of 1 ‐ substituted arylpyrroles is clearly shown in the Scheme 195.…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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A solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas protocol for the synthesis of N‐aryl pyrroles under microwave irradiation

Rohit

Meera

Anilkumar

2021

Journal of Heterocyclic Chem

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The first manganese‐catalyzed modified Clauson‐Kaas reaction for N‐substituted pyrrole synthesis using 2,5‐dimethoxytetrahydrofuran with variously substituted aromatic amines has been developed (up to 89% yield). This interesting neat strategy is free from additives including co‐catalysts, ligands, and acids. Relatively low cost, environmentally benign, and handy Mn(NO3)2·4H2O is employed as the catalyst under microwave conditions with a very short reaction time (20 min). The above qualities attest to the green nature of this reaction.

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A facile synthesis of 1-aryl pyrroles by Clauson-Kaas reaction using oxone as a Catalyst under microwave irradiation

Cited by 11 publications

References 25 publications

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

A solvent‐free manganese(II) ‐catalyzed Clauson‐Kaas protocol for the synthesis of N‐aryl pyrroles under microwave irradiation

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