Bicyclic 5-6 Systems: Two Heteroatoms 1:1

Sherman, Angela R.

doi:10.1016/b978-008044992-0.00906-8

Cited by 8 publications

(3 citation statements)

References 483 publications

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“…Furo[3,2- c ]pyridines play an important role in organic chemistry for their presence in numerous natural products and synthetic organic compounds along with diverse bio-, physio-, and pharmacological activities. , In addition, furo[3,2- c ]pyridines are common organic ligands in transition metal complexes . Extensive work has generated many synthetic approaches to furo[3,2- c ]pyridine derivatives, starting either from preformed furans or pyridines. , However, most of the existing methods require multistep procedures to generate the pyridine and furan rings individually, and suffer from limited substrate scope and harsh reaction conditions. So far, there are only very few methods reported on the synthesis of furo[3,2- c ]pyridines by construction of the furan and pyridine nuclei in a single step .…”

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confidence: 99%

[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

et al. 2012

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Two novel routes based on [5C + 1N] annulations for the synthesis of 2,3-dihydrofuro[3,2-c]pyridines are described. Ammonium acetate (NH(4)OAc) is used as an ammonia source in both routes. The first route utilizes 1-acyl-1-[(dimethylamino)alkenoyl]cyclopropanes as a five-carbon 1,5-bielectrophilic species and combines the [5C + 1N] annulation and regioselective ring-enlargement of cyclopropyl ketone into one pot, whereas the second route utilizes 3-acyl-2-[(dimethylamino)alkenyl]-4,5-dihydrofurans as the five-carbon synthons, which involves a sequential intermolecular aza-addition, intramolecular aza-nucleophilic addition/elimination, and dehydration reaction.

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confidence: 99%

[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

et al. 2012

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“…The antihypertensitive drug cicletanine is a furo [3,2c]pyridine derivative. The furopyridine skeleton from which this compound is derived is not associated with any known pharmacological classes (SHERMAN, 1996).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and reactions of [1]benzofuro[3,2-c]pyridine

Juristová

Štefanovová

Ďurčeková

et al. 2022

Nova Biotechnol. Chim.

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(E)-3-(1-Benzofuran-2-yl)propenoic acid (I) was prepared from 1-benzofuran-2-carbaldehyde under the Doebner’s conditions. The obtained acid was converted to the corresponding azide II, which was cyclized by heating in diphenyl ether to [1]benzofuro[3,2-c]pyridin-1(2H)-one (III). This compound was aromatized with phosphorus oxychloride to chloroderivative IV which was reduced with zinc and acetic acid to the title compound V. [1]Benzofuro[3,2-c]pyridin-2-oxide (VI) was synthesized by reaction of V with 3-chloroperoxybenzoic acid in dichloromethane. Treatment VI with benzoyl chloride and potassium cyanide (Reissert-Henze reaction) was shown to produce the corresponding [1]benzofuro[3,2-c]pyridin-1-carbonitrile (VII). The title compound was used for preparation of complex compounds VIII, IX

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“…The formation kinetics of the bis-aryl hydrazone bond are 20 to 900 times higher than those of conventional hydrazone/oxime bonds between alkyl aldehydes/ ketones and alkyl hydrazide or aminoxy probes. 14 The hydrazide hydrazones have been demonstrated to possess antibacterial, [15][16][17] anticonvulsant [18][19][20] and antitubercular 21 activities. Furthermore, the benefits of click reactions are well-known, and their applications have revolutionized numerous fields including bioconjugate chemistry, material chemistry and polymer sciences.…”

Section: Introductionmentioning

confidence: 99%

Facile green synthesis and potent antimicrobial efficacy of β-aminoheteronapthol via tailored Betti’s protocol and their bis-aryl hydrazone click products

Khandarkar

Shanti

Ahmed³

et al. 2013

J Chem Sci

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A series of novel Mannich base and their hydrazone derivatives were synthesized by highly resourceful, chic, simple and green technique with exceptionally facile reaction conditions of one-pot, three component reaction with an array of biologically and pharmaceutically active novel heterocycles. The protocol offers a valuable alternative to known methods and will find applications in the field of green synthesis and antimicrobial study against pathogenic microbes, supporting the development of bioinformatical database of novel and derelict heterocycles. These data indicate their potential to become antifungal agents. The novel products were established by elemental, IR, mass spectroscopic and NMR analysis. The environmental advantages of the method include short reaction time, excellent yield, easy work-up, absence of extraction and chromatographic purification steps.

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Bicyclic 5-6 Systems: Two Heteroatoms 1:1

Cited by 8 publications

References 483 publications

[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

[5C + 1N] Annulations: Two Novel Routes to Substituted Dihydrofuro[3,2-c]pyridines

Synthesis and reactions of [1]benzofuro[3,2-c]pyridine

Facile green synthesis and potent antimicrobial efficacy of β-aminoheteronapthol via tailored Betti’s protocol and their bis-aryl hydrazone click products

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