Ultrasound Promoted Synthesis of 2-Amino-4-H-Pyranoquinolines Using Sulphated Tin Oxide as a Catalyst

Koduri, Ramesh Goud; Pagadala, Ramakanth; Boodida, Sathyanarayana; Varala, Ravi

doi:10.1080/10406638.2021.1992456

Cited by 7 publications

(4 citation statements)

References 39 publications

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“…As a continuance of Scheme 21, numerous substituted benzaldehyde compounds were available, and these were used to successfully synthesis the various pyranoquinoline derivatives ( 41a–f ). For the production of bioactive pyranoquinoline variants in an appropriate reaction environment with minimal reaction time, simple blending and separating with appropriate yield, and regenerated and reused catalyst, this is unquestionably a leading sustainable method (Figure 7) [28].…”

Section: Synthesis Strategies For Pyranoquinolone Derivatives and The...mentioning

confidence: 99%

“…As ubiquitous substructures in biologically beneficial natural products, quinoline compounds play an important role in medicinal chemistry [22,23]. Instead of this, the pyran moiety is found throughout natural food [24,25], and plays an important role in the synthesis of drugs such as those that fight cancer and HIV as well as those that help lower cholesterol and fight diabetes [26][27][28][29][30]. One of the most interesting nitrogenous heterocycles are these molecules.…”

Section: Introductionmentioning

confidence: 99%

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Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Uppal

Mir

Chawla

et al. 2022

Journal of Heterocyclic Chem

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The search for new heterocyclic compounds with potential bioactivities continues despite the fact that extensive work has already been done on pyranoquinolones. Researchers throughout the world have used the pyranoquinolone nucleus extensively to generate a wide variety of bioactive heterocycles that target a wide spectrum of biological targets. An in-depth investigation into possible pyranoquinolone derivatives and their pharmacological importance is the focus of this overview of synthetic techniques. Researchers and medicinal chemists can benefit from this review by developing new pyranoquinolone nucleus leads that are very effective and have fewer adverse effects than existing ones.

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Section: Synthesis Strategies For Pyranoquinolone Derivatives and The...mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Uppal

Mir

Chawla

et al. 2022

Journal of Heterocyclic Chem

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“…5 Varala et al have recently developed ultrasound irradiated synthesis of 2-amino-4H-pyranoquinolines in excellent yields using heterogeneous reusable STO as catalyst in ethanol at 60 °C, from different aldehydes, malononitrile and 8-hydroxyquinoline (Scheme 1). 6 The strategy followed in this method gives an additional feature like, easy setup, less reaction time, effortless decantation, good yields and consequently create an utmost contribution to green chemistry.…”

Section: -1-1 Synthesis Of 2-amino-4h-pyranoquinolinesmentioning

confidence: 99%

Applications of Sulfated Tin Oxide (STO) in Organic Synthesis - from 2016 to 2021

Varala¹,

Dubasi²

2022

HETEROCYCLES

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In this mini-review, authors have briefed about the applications of sulfated tin oxide (STO) as bifunctional catalyst in various C-C, C-hetero bond formations. Synthesis of biologically relevant pyranoquinolines, benzimidazoles, benzodiazepines, fully substituted pyridines, dihydropyridines and isoxazoles were performed by heterogeneous recyclable and reusable solid acid catalyst, STO. In addition, methodologies such as N-Boc protection of amines, production of renewable less viscous, high-density fuel molecules from α-pinene, selective production of MeCl from CH4, esterification, tert-butylation and conversion of glucose into value added 5-hydroxymethylfurfural, were established by using STO as catalyst. CONTENTS 1. Introduction 2. Recent applications of STO (During 2016-2021) 2-1. Synthesis of Heterocycles 2-1-1. Synthesis of 2-amino-4H-pyranoquinolines 2-1-2. Synthesis of 1,4-dihydropyridine derivatives 2-1-2-1. Varala and co-workers 2-1-2-2. Munde and co-workers 2-1-3. Synthesis of fully functionalized pyridines 2-1-4. Synthesis of benzimidazoles 2-1-5. Synthesis of 1,5-benzodiazepine derivatives 2-1-6. Synthesis of 4-arylmethylidene-3-substituted-isoxazol-5(4H)-ones 2-2. Miscellaneous reactions 2-2-1. Coupling reactions of α-pinene to produce dimeric hydrocarbon products (fuels) 2-2-2. N-Boc (N-tert-butoxycarbonyl) protection of aliphatic, aromatic and cyclic amines 2-2-3. Gas phase catalytic chlorination of CH4 2-2-4. Esterification of levulinic acid 2-2-5. Esterification of propionic acid 2-2-6. tert-Butylation of phenol 2-2-7. Esterification of free fatty acids (FFA) 2-2-8. Conversion of D-glucose to 5-hydroxymethylfurfural (HMF) 3. Conclusion

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“…Due to its low cost, greater stability, non-corrosive nature, reuse and recyclability, high efficiency, and large surface area, sulfated tin oxide (STO, SO4 -2 /SnO2) has emerged as an effective and commercial catalyst. It is used extensively in chemical and industrial applications, [29][30][31][32][33][34][35][36] consisting of both sulfated and sulfonic acid moiety on heterogeneous solid bases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions

Krishna,

Seetharam,

Satyadev

2024

10.5267/j.ccl

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One significant and elegant method for creating β-amino alcohols, which are useful intermediates for the synthesis of many different natural and synthetic pharmaceutical compounds, is to open the rings of epoxides with amines. When sulfated tin oxide catalyst (2 mol%) is present, epoxides can open their rings and react with amines to produce corresponding β-amino alcohols in good to high yields under mild circumstances. Under clean circumstances and in a short amount of time, the reaction demonstrated high regioselectivity and functioned well with both aromatic and aliphatic amines at room temperature.

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Ultrasound Promoted Synthesis of 2-Amino-4-H-Pyranoquinolines Using Sulphated Tin Oxide as a Catalyst

Cited by 7 publications

References 39 publications

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Pyranoquinolone derivatives: A potent multi‐targeted pharmacological scaffold

Applications of Sulfated Tin Oxide (STO) in Organic Synthesis - from 2016 to 2021

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions

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