Synthesis and antimicrobial activity of substituted 4H-pyrano- and dihydropyrano[3,2-d]pyrazoles

Mityurina, K. V.; Kulikova, L. K.; Krasheninnikova, M. K.; Харченко, В. Г.

doi:10.1007/bf00758668

Cited by 7 publications

(3 citation statements)

References 2 publications

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“…Some heterocyclic compounds containing condensed pyrazoles such as pyrano [2,3-c]pyrazoles possess a wide spectrum of pharmacological action, including analgesic, anti-inflammatory, vasodilating, and antihypertensive activities. [38][39][40] Hence, the preparation and biological properties of new substituted pyrano [2,3-c]pyrazoles are interest. [41][42][43][44][45][46][47][48][49][50] To check something about reactivity of SPOs 2, we examined a ring transformation of SPOs 2a-d into pyrano [2,3-c]pyrazoles.…”

Section: Synthesis and Application Of Spos Containing Cyclopropane Mo...mentioning

confidence: 99%

Spiro Heterocycles: Synthesis and Application of Spiro Pyrazol-3-one Derivatives

Mikami¹,

Masumoto²

2022

HETEROCYCLES

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Spiro compounds play an important role in organic chemistry, not only as key structural units in many natural products and pharmaceuticals but also as useful building blocks in synthetic chemistry. This review deals with the synthesis and application of spiro heterocycles, especially spiro pyrazol-3-ones (SPOs). SPOs represent a common scaffold present in a wide range of biological active compounds, such as antibacterial, analgesic, phosphodiesterase, inotropic, acetyl-CoA carboxylase, PPARa, RaIA, and antitumor activities, among others. The structural features of SPOs provide them with increased reactivity, and SPOs undergo a series of interesting reactions under appropriate conditions, giving efficient methods for the construction of many useful organic compounds. The exploration of SPOs novel reaction has attracted much attention of organic chemists. Generally, SPOs reaction types include nucleophilic addition, ring-opening, and ring transformation reactions. The present review summarizes the advances on SPOs during the period of 2008 to 2021 in our laboratory. CONTENTS 1. Introduction 2. Synthesis and Application of SPOs Containing Cyclopropane Moiety 3. Synthesis and Application of SPOs Containing Oxirane Moiety 4. Synthesis and Application of SPOs Containing Isoxazoline Moiety 5. Synthesis of SPOs Containing Iminolactone and/or Cyclic Imide Moiety 6. Synthesis of SPOs Containing Quinazoline Moiety 7. Synthesis and Application of SPOs Containing Cyclobutathiazole Moiety 8. Conclusion

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Section: Synthesis and Application Of Spos Containing Cyclopropane Mo...mentioning

confidence: 99%

Spiro Heterocycles: Synthesis and Application of Spiro Pyrazol-3-one Derivatives

Mikami¹,

Masumoto²

2022

HETEROCYCLES

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“…In recent years, they have attracted attention of synthetic organic chemists because of their presence in many bioactive compounds. These molecules demonstrate versatile activities like fungicide, AMPA receptor activity enhancer, antitubercular, antimicrobial, antibacterial, and human Chk1 kinase inhibitory properties, among others. (Figure ).…”

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confidence: 99%

Organocatalytic Asymmetric Inverse-Electron-Demand Diels–Alder Reaction between Alkylidene Pyrazolones and Allyl Ketones: Access to Tetrahydropyrano[2,3-c]pyrazoles

2023

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Herein we report a catalytic asymmetric inverse-electron-demand Diels–Alder reaction between alkylidene pyrazolones and allyl ketones. Allyl ketone gets activated by a bifunctional thiourea catalyst and acts as a dienolate in this reaction. The trisubstituted tetrahydropyrano[2,3-c]pyrazoles were obtained in moderate to good yields with high diastereo- and enantioselectivities. Few applications, including a decarbonylation reaction, have been demonstrated.

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“…Pyrano[2,3- c ]pyrazoles, important structural heterocyclic motifs of fused pyranones and pyrazolones, have attracted the attention of synthetic organic chemists since they are an abundant source of biologically active molecules . These motifs possess fungicide, AMPA receptor activity enhancer property, antitubercular, antimicrobial, antibacterial, and human Chk1 kinase inhibitory properties (Figure ). Because of the pharmaceutical importance of pyranopyrazoles, many research groups put their efforts for the synthesis of functionalized pyrano[2,3- c ]pyrazoles, and a number of useful strategies have been developed in recent years .…”

mentioning

confidence: 99%

DMAP Catalyzed Domino Rauhut–Currier Cyclization Reaction between Alkylidene Pyrazolones and Nitro-olefins: Access to Tetrahydropyrano[2,3-c]pyrazoles

et al. 2021

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Herein, we employ unsaturated pyrazolones in the Rauhut–Currier reaction for the first time. A domino Rauhut–Currier cyclization reaction has been developed between unsaturated pyrazolones and nitro-olefins. The trisubstituted tetrahydropyrano[2,3-c]pyrazoles were obtained in moderate to high yields with excellent diastereoselectivities. A few applications including a synthesis of disubstituted tetrahydropyrano[2,3-c]pyrazole have been demonstrated. A preliminary catalytic asymmetric version of this process was also studied with chiral DMAP catalysts.

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Synthesis and antimicrobial activity of substituted 4H-pyrano- and dihydropyrano[3,2-d]pyrazoles

Cited by 7 publications

References 2 publications

Spiro Heterocycles: Synthesis and Application of Spiro Pyrazol-3-one Derivatives

Spiro Heterocycles: Synthesis and Application of Spiro Pyrazol-3-one Derivatives

Organocatalytic Asymmetric Inverse-Electron-Demand Diels–Alder Reaction between Alkylidene Pyrazolones and Allyl Ketones: Access to Tetrahydropyrano[2,3-c]pyrazoles

DMAP Catalyzed Domino Rauhut–Currier Cyclization Reaction between Alkylidene Pyrazolones and Nitro-olefins: Access to Tetrahydropyrano[2,3-c]pyrazoles

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