An Efficient and Novel Regioselective Synthesis of Phosphonylpyrazoles from Vinylazides and Bestmann-Ohira Reagent

Madugula, Aravinda Kumar; Mahendran, V.; Sridhara, A. M.; Rangaiah, G. Subba

doi:10.13005/ojc/320524

Cited by 9 publications

(6 citation statements)

References 3 publications

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“…Rangaiah and his team reported a novel synthetic methodology for the construction of phosphonyl pyrazoles 129 using base‐mediated 1, 3‐cycloaddition reaction of α ‐azidochalcones 1 and Bestmann‐Ohira reagent (BOR) 130 in MeOH at ambient temperature (Scheme 24). [54] …”

Section: Thermal Reactions Of α‐Azidochalconesmentioning

confidence: 99%

Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis

Devi Newar,

Jyoti Boruah,

Awatar Maurya

2024

Adv Synth Catal

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α‐Azidochalcones have emerged as remarkably versatile precursors within organic azides, showcasing a broad spectrum of reactivity as a cornerstone for synthesizing diverse molecular scaffolds. The ongoing progress in this field has opened new opportunities for constructing complex organic molecules through diverse chemical transformations due to the versatile reactivity of α‐azidochalcones for further functionalization. The comprehensive review presented herein provides a concise yet detailed examination of the synthesis, reactivity, and potential applications of α‐azidochalcones. Focusing on both thermal and photochemical pathways, this review highlights the versatility of α‐azidochalcones as pivotal precursors in the synthesis of various heterocyclic frameworks.

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Section: Thermal Reactions Of α‐Azidochalconesmentioning

confidence: 99%

Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis

Devi Newar,

Jyoti Boruah,

Awatar Maurya

2024

Adv Synth Catal

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“…Jiang and co-workers synthesized various benzyl-linked indole-C2 pyrazole hybrids (65-67) and pyrazole-bearing benzo[b]carbazolones (70)(71)(72)(73)(74) as illustrated in Schemes 11 & 12, and studied their anaplastic lymphoma kinase (ALK) inhibitory activities. [49] The intermediate, tert-butyl 6-cyano-2-(2-(4-ethyl-3-iodophenyl)propan-2-yl)-1H-indole-3-carboxylate (64) was prepared starting from ethyl (2-(4-ethyl-3-iodophenyl)-2methylpropanoyl)carbamate ( 63) by following the literature procedure.…”

Section: Aryl/heteryl-linked Indole-c2 Pyrazole Hybridsmentioning

confidence: 99%

“…The advantages of this methodology include high yields of the products formed in relatively shorter reaction times, use of relatively mild reaction conditions, and easy workup and column-free purification of the products. [73] Hemamalini and co-workers synthesized several sugarcontaining pyrazole derivatives (169) in good yields (70-84 %) (Scheme 30). The α,β-unsaturated-C-β-glycosidic ketones (168) were obtained by Aldol condensation of C-β-glycosidic ketone (167) with various aryl aldehydes and heteryl aldehydes including indol-3-yl and polycyclic aryl aldehydes in the presence of pyrrolidine as a base at room temperature.…”

Section: Chemistryselectmentioning

confidence: 99%

“…They were synthesized via the 1,3‐dipolar cycloaddition reaction between indole‐containing vinyl azide ( 164 a – c ) and dimethyl (1‐diazo‐2‐oxopropyl)phosphonate (Bestmann‐Ohira reagent, 165 ) in the presence of KOH. The advantages of this methodology include high yields of the products formed in relatively shorter reaction times, use of relatively mild reaction conditions, and easy workup and column‐free purification of the products [73] …”

Section: Direct‐linked Indole‐c3 Pyrazole Hybridsmentioning

confidence: 99%

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Recent Developments in the Synthesis of Indole‐Pyrazole Hybrids

et al. 2022

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Indole and pyrazole are two important scaffolds in the field of medicinal chemistry. Compounds bearing indole and/or pyrazole moiety have been extensively investigated for a wide range of biological applications. Of them, compounds containing both indole and pyrazole moieties (also termed as indole‐pyrazole hybrids) are of particular interest since synergistic pharmacological activities may be gained comparing to those with each individual pharmacophore. Indole‐pyrazole hybrids can be classified into two general classes of direct‐linked hybrids and spacer‐linked hybrids. For each class, it can be sub‐divided into indole‐C2 pyrazole hybrids, indole‐C3 pyrazole hybrids and indole‐C4/5/6/7 pyrazole hybrids based on the substitution position of pyrazole on the indole moiety. Many types of indole‐pyrazole hybrids have been reported with good antimicrobial, anticancer, antitumor, anti‐inflammatory, anti‐oxidant activities etc. However, no papers have been noted to comprehensively summarize the chemical synthesis of these important indole‐pyrazole hybrids as bioactive compounds except for a few reviews focusing on the synthesis of each individual indole‐ and pyrazole‐containing derivatives. Thus, we here present a comprehensive and updated review focusing on the progress of chemical synthesis of all types of indole‐pyrazole hybrids in order to provide a better understanding of the indole‐pyrazole hybrids to researchers in the fields of synthetic chemistry and to facilitating drug development.

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“…The transformation proceeds through 1,3-dipolar cycloaddition at room temperature in moderate to good yields (Scheme 32). 40…”

Section: Scheme 31mentioning

confidence: 99%

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

et al. 2019

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Indolylvinyl ketones are valuable building blocks that can be utilized for the synthesis of numerous natural products and bioactive molecules containing an indole core motif. Herein, we describe their application for the total synthesis of some alkaloids, their analogues, and a variety of other important compounds, with an emphasis on biologically active examples.1 Introduction2 Functionalization of the Enone C=C Bond2.1 Reduction2.2 Michael Addition2.3 Cycloaddition3 Transformation of the Carbonyl Group3.1 Reduction3.2 Knoevenagel Reaction3.3 Addition of Organometallic Compounds3.4 Olefination4 Reactions Involving the Enone Conjugate System С=С–С=О4.1 Reactions with 1,2-Dinucleophiles4.2 Reactions with Compounds Bearing an Active Methylene Group4.3 Reactions with 1,3-Dinucleophiles4.4 Reactions with 1,4-Dinucleophiles5 Functionalization of the Enone Methylene Group C(O)–CH2R5.1 Acylation/Crotonic Condensation and Related Transformations5.2 Enolization6 Functionalization of the Indole Core6.1 [4+2] Cycloaddition6.2 [3+3] Annulation6.3 Electrocyclic Reactions7 Miscellaneous8 Conclusions

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An Efficient and Novel Regioselective Synthesis of Phosphonylpyrazoles from Vinylazides and Bestmann-Ohira Reagent

Cited by 9 publications

References 3 publications

Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis

Recent Advances in the Use of α‐Azidochalcones in Heterocycle Synthesis

Recent Developments in the Synthesis of Indole‐Pyrazole Hybrids

Indolylvinyl Ketones: Building Blocks for the Synthesis of Natural Products and Bioactive Compounds

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