One-pot synthesis of thieno [2,3-d] pyrimidin-4-ol derivatives mediated by polyphosphonic anhydride

Poojari, Subba; Naik, P. Parameswar; Krishnamurthy, G.

doi:10.1016/j.tetlet.2012.06.017

Cited by 19 publications

(6 citation statements)

References 24 publications

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“…In continuation of our research work on the applications of T3P s in several organic transformations 13 and novel methods for amide synthesis, 14 we report herein an efficient and solvent free T3P s -mediated amidation of benzhydrols with poorly reactive N-nucleophiles such as amides, sulfonamides and carbamates under microwave conditions. Recently, T3P s has been demonstrated to be a useful reagent in many synthetic applications like condensations reactions, 15 cyclization reactions, 16 reduction of acids to alcohols 17 and peptide coupling reactions 18 due to its reduced epimerization, excellent reaction selectivity, low cost and less toxicity. 19,20 More importantly, the by-product from the reagent is highly water-soluble which facilitates hassle-free large-scale synthesis.…”

Section: Andmentioning

confidence: 99%

An expedient, efficient and solvent-free synthesis of T3P®-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation

Cheruku

Sandhya²,

Narayana

et al. 2022

New J. Chem.

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Section: Andmentioning

confidence: 99%

An expedient, efficient and solvent-free synthesis of T3P®-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation

Cheruku

Sandhya²,

Narayana

et al. 2022

New J. Chem.

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“…Using a phosphine reagent (ClP(Bin), PPh 3 ,– PO(osalMe) 3 , polyphosphonic anhydride), arylacetic acids would convert into intermediates 42.1 as a powerful electrophile. 42.1 easily reacted with weak nucleophiles (tertiary amine, THF, styrene episulfide, F‐) to yield aimdes 42.3, esters 42.6 , thioesters 42.7 , 42.8 and acyl fluorides 42.5 (Eq.…”

Section: Nucleophilic Acidsmentioning

confidence: 99%

Arylacetic Acids in Organic Synthesis

et al. 2019

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Arylacetic acids are widely used in organic reactions and their recent advances are summarized in six categories according to their triggered pathways: (1) the acid as directing group in ortho-or meta-CÀ H activation; (2) decarboxylation; (3) deprotonation; (4) nucleophilic methylenes; (5) nucleophilic acids; (6) electrophilic acids. Reactions with alkenes, alkynes, aldehydes, amines, water, Grignard reagents, silanes and so forth are discussed. We hope this Minireview will promote future research in this area. Recently, the Zeng group [3g] reported a weakly coordinationassisted alkynylation of arylacetic acids with iridium catalysis under air atmosphere (Eq. 2-2). It was supported the sixmembered ring cycloiridiated 2.5 acted as the key intermediate. The alkynylation of indole, thiophene, pyrrole, and benzo[b] thiophene afforded better yields than phenylacetic acids. The acid moiety could also participated in the intramolecular ortho-CÀ H activation, which was developed by the Shi group to obtain lactonization 2.6 (Eq. 2-3) (Scheme 2). Meta-CÀ H ArylationThe study of Yu group [3e] in 2017 revealed a successful control of meta selectivity 3.1 of arylation from aryl iodides (Eq. 3-1). The use of mono-protected 3-amino-2-hydroxypyridine (as ligand) and 2-carbomethoxynorbornene (NBE-CO 2 Me) were crucial. In the absence of NBE-CO 2 Me, only ortho-arylated product was obtained. This method was still efficient in a gramsale (Scheme 3). Decarboxylation Decarboxylative CouplingAs shown in Scheme 4, the decarboxylation could generate benzyl radicals 4.1. Then, direct couplings of 4.1 with diverse [ + ] These authors contributed equally. Scheme 1. Six categories based on triggered mechanism. 2 3 4 5 6 7 8 . Passerini Three-Component ReactionThe Passerini reaction was the oldest multicomponent reaction (MCR) [37d] in which isocyanides, carboxylic acids and aldehydes were used. It was powerful for the rapid construction of complex molecules. The tactic to expand the scope of Passerini reaction was to use surrogates of the carbonyl partners. As described in Scheme 51, syn-chlorooximes, [37b] diazoketones, [37c] alcohols, [37d,e] azirines [37f] and isatins [37g] could be employed instead of aryl or alkyl aldehydes [37a] (Scheme 51). Besides, in 2018, Zhang and co-workers [37] have firstly reported asymmetric phosphoric acid-catalyzed four-component Ugi reaction, which Scheme 45. BTM-catalyzed cycloaddition. Scheme 46. HBTM-catalyzed cycloaddition. Scheme 47. TFA-catalyzed reaction. Scheme 48. Friedel-Crafts triggered tandem reactions. Scheme 49. C-acylation of 1,3-diones. Scheme 50. C-acylation of 1,3-indandiones.

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“…In this respect, we have reported the synthesis of macrocycles containing 1,3,4-oxadiazole and pyridine moieties as well as a number of pyrimidin-4-ol derivatives [24,25]. In the present work, extensive efforts have been made to design and synthesize novel quinazolinone hybrids via introducing amide, urea, and sulfonamide systems with different possible functionalities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Studies of New Spiropyran Quinazolinone Derivatives with Amide, Urea, and Sulfonamide Moieties

Poojari

Krishnamurthy

et al. 2017

Journal of Heterocyclic Chem

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Three new series of quinazolinone derivatives containing amide, urea, and sulfonamide were synthesized through multistep synthesis. The required intermediates 4‐[(4′‐oxo‐2,3,3′,4′,5,6‐hexahydro‐1′H‐spiro[pyran‐4,2′‐quinazolin]‐1′‐yl)methyl]benzoic acid 4 and 1′‐(3‐aminobenzyl)‐2,3,5,6‐tetrahydro‐1′H‐spiro[pyran‐4,2′‐quinazolin]‐4′(3′H)‐one 8 were prepared by hydrolysis of ester and reduction of nitro intermediates. Three different series of compounds were synthesized from these two scaffolds. The key scaffolds 4 and 8 were successfully converted to target molecules via amides 5a–k, urea 9a–f, and substituted sulfonamides 10a–e. The chemical structures of newly synthesized compounds were characterized by spectral analysis. The structure of 5d was confirmed by X‐ray crystallography study. These newly synthesized compounds were screened for antibacterial studies against Staphylococcus epidermidis, Salmonella typhi, Proteus mirabilis, and Shigella sonnei and for the antifungal activity against Aspergillus niger and Candida albicans. Among all the compounds, 9b–d showed excellent activities against S. typhi. Compound 9a showed moderate activity against all fungi stains, and 5I showed moderate activity against P. mirabilis, while the other derivatives showed fairly good activities.

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One-pot synthesis of thieno [2,3-d] pyrimidin-4-ol derivatives mediated by polyphosphonic anhydride

Cited by 19 publications

References 24 publications

An expedient, efficient and solvent-free synthesis of T3P®-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation

An expedient, efficient and solvent-free synthesis of T3P®-mediated amidation of benzhydrols with poorly reactive N-nucleophiles under MW irradiation

Arylacetic Acids in Organic Synthesis

Synthesis and Antimicrobial Studies of New Spiropyran Quinazolinone Derivatives with Amide, Urea, and Sulfonamide Moieties

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