Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

Dandia, Anshu; Singh, Ruby; Joshi, Jyoti; Maheshwari, Shuchi; Soni, Pragya

doi:10.1039/c3ra43745k

Cited by 39 publications

(11 citation statements)

References 64 publications

(8 reference statements)

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“…Hence, inspired by these findings and in continuation of our ongoing work to develop environmentally benign methodologies [54][55][56][57][58][59][60][61] for the synthesis of biologically useful heterocycles, we have investigated a threecomponent protocol for the synthesis of drug-like spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones from the multi-component reaction of acenapthaquinone, substituted anilines, and a-mercaptoacetic acid in good yield using thiamine hydrochloride as a green, inexpensive, and reusable catalyst in aqueous medium. The present method is more convenient and efficient because it obviates the azeotropical removal of water and use of carcinogenic solvents as well as dehydrating agents.…”

Section: Introductionmentioning

confidence: 86%

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

Singh

Ganaie

2016

Res Chem Intermed

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A water mediated and thiamine hydrochloride catalysed eco-compatible efficient method was developed for the synthesis of spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones via multi-component reaction of acenaphthylene-1,2-dione, substituted anilines, and a-mercaptocarboxylic acid at 80°C temperature. This transformation involves the formation of two C-N bonds and one C-S bond leading to the creation of a five-member ring in a one-pot operation. Easy availability and recovery of the catalyst, no toxic/organic solvents, and high yield of product make the protocol attractive, sustainable, and economic. Graphical AbstractO O NH 2 1 2 HS O OH 3 O N S O R 1 R 1 R R R 1 = H, CH 3

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Section: Introductionmentioning

confidence: 86%

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

Singh

Ganaie

2016

Res Chem Intermed

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“…Despite their importance, most processes for their synthesis require harsh conditions, expensive reagents, high catalyst loading, corrosive or toxic reagents, and often lead to several side reactions [52]. In 2013, Dandia et al [53] developed a three-component reaction under catalyst-free conditions and ultrasonic irradiation for the synthesis of spiro[indole-3,4 -pyrazolo[3,4-e] [1,4]thiazepines] in water. The reaction was shown to be chemo-, regio-, and diastereo-selective, and the formation of the thiodiazepin seven-membered ring was conditioned by that of a Baylis-Hillman type adduct (Scheme 11).…”

Section: Of 35mentioning

confidence: 99%

Ultrasound for Drug Synthesis: A Green Approach

2020

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This last century, the development of new medicinal molecules represents a real breakthrough in terms of humans and animal life expectancy and quality of life. However, this success is tainted by negative environmental consequences. Indeed, the synthesis of drug candidates requires the use of many chemicals, solvents, and processes that are very hazardous, toxic, energy consuming, expensive, and generates a large amount of waste. Many large pharmaceutical companies have thus moved to using green chemistry practices for drug discovery, development, and manufacturing. One of them is the use of energy-efficient activation techniques, such as ultrasound. This review summarizes the latest most representative works published on the use of ultrasound for sustainable bioactive molecules synthesis.

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“…This transformation involves the generation of two rings and five new bonds (two C-C, two C-N and one C=N) in a single synthetic operation (Scheme 34). The synthesis of spiroacenaphthylene pentacyclic system 105 in 65% yield from the one-pot reaction of 1, cyclic ketone 106, and two molecules of malononitrile (71) in the presence of morpholine as the catalyst at ambient temperature for 5 minutes was reported by Elinson and co-workers (Scheme 37). 51…”

Section: Scheme 33mentioning

confidence: 99%

“…In another report, Bazgir et al 34 synthesized spiroacenaphthylene-pyrano[2,3-c]pyrazole 80 in 87% yield using piperidine as the catalyst in a four-component reaction of β-keto ester 81, hydrazine hydrate (76), malononitrile (71) and 1 in aqueous medium for 5 hours. Most of the products exhibited good to excellent antibacterial activities.…”

Section: Scheme 27 Synthesis Of Spirodihydropyridine Derivatives 78mentioning

confidence: 99%

“…Dandia et al 71 have synthesized spirothiazepines 141 in 90-91% yields by multicomponent domino reactions of 5aminopyrazole (142), α-mercaptocarboxylic acids 143 and 1 in aqueous medium under ultrasonic irradiation for 20 minutes (Scheme 51). This new and green protocol provides a novel seven-membered-ring system instead of the expected five-membered ring or other possible isomers, without the addition of any acid or base catalyst.…”

Section: Scheme 50 Synthesis Of 1′h2h-spiro[acenaphthylene-12′-quinmentioning

confidence: 99%

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Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

Yavari

Khajeh-Khezri²

2018

Synthesis

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Acenaphthylene-1,2-dione has been utilized in a wide range of reactions as a starting material for the synthesis of hetero- and carbocyclic compounds and complexes. This review provides a short summary of the recent advances in the application of acenaphthylene-1,2-dione in the synthesis of hetero- and carbocyclic systems and bioactive compounds. In addition, the applications of acenaphthylene-1,2-dione in the synthesis of spiro compounds, propellanes, and ligands in catalyst reactions, from 2002 to early 2018, are included.1 Introduction2 Synthesis of Spiro Compounds Employing Acenaphthylene-1,2-dione2.1 Methods for the Construction of Spiro Compounds2.1.1 By 1,3-Dipolar Cycloaddition of Acenaphthylene-1,2-dione via Azomethine Ylides2.1.2 By Multicomponent Reactions of Acenaphthylene-1,2-dione with C–H Acidic Compounds2.1.3 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates2.1.4 By Substitution and Multicomponent Reactions of Acenaphth- ylene-1,2-dione with Different Nucleophiles3 Synthesis of Propellanes by Employing Acenaphthylene-1,2-dione3.1 Methods for the Construction of Propellanes Based on Acenaph- thylene-1,2-dione3.1.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles3.1.2 By Reaction of Acenaphthylene-1,2-dione with Binucleophiles4 Synthesis of Ligands Employing Acenaphthylene-1,2-dione for Catalyst Reactions5 Synthesis of Novel Hetero- and Carbocyclic Compounds Employing Acenaphthylene-1,2-dione5.1 By Reaction of Acenaphthylene-1,2-dione with Nucleophiles5.2 By Reaction of Acenaphthylene-1,2-dione with Zwitterionic Intermediates5.3 By Ring Opening and Ring Enlargement6 Conclusion

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Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

Cited by 39 publications

References 64 publications

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

Ultrasound for Drug Synthesis: A Green Approach

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione

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Ultrasound promoted catalyst-free and selective synthesis of spiro[indole-3,4′-pyrazolo[3,4-e][1,4]thiazepines] in aqueous media and evaluation of their anti-hyperglycemic activity

Cited by 39 publications

References 64 publications

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

Ultrasound for Drug Synthesis: A Green Approach

Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds­ and Complexes Based on Acenaphthylene-1,2-dione

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Recent Advances in the Synthesis of Hetero- and Carbocyclic Compounds and Complexes Based on Acenaphthylene-1,2-dione