Preparation of 1-amidoalkyl-2-naphthol derivatives using barium phosphate nano-powders

Taghrir, Hadi; Ghashang, Majid; Biregan, Mohammad Najafi

doi:10.1016/j.cclet.2015.08.011

Cited by 51 publications

(13 citation statements)

References 39 publications

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“…So, progress in the synthetic methodology for preparation of 1‐amidoalkyl‐2‐naphtols is great demand. Various methods have been reported for the synthesis of these compounds in the presence of different catalysts such as [Msim]Cl, TrCl, ethylammonium nitrate (EAN), thiamine hydrochloride, nickel‐doped SnO 2 nanoparticles, montmorillonite K10, Ba 3 (PO 4 ) 2 nanopowders, HClO 4 ‐SiO 2 , P 2 O 5 , iodine, p ‐TSA, K 5 CoW 12 O 40 .3H 2 O, silica sulfonic acid and Fe(HSO 4 ) 3 . Some of these methods suffer from drawbacks such as long reaction times, use of toxic reagents, tedious work‐up and low yield of products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Nanomagnetic Catalyst with Acetic Acid Tags: Application in the Synthesis of New Amidoalkyl Phenols under Solvent‐Free Condition

et al. 2019

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In this paper, [Fe3O4@SiO2@(CH2)3‐im‐CH2CO2H]Br was designed, synthesized and fully characterized by different techniques such as Fourier transform spectroscopy infrared (FT‐IR), scanning electron microscopy (SEM), energy‐dispersive X‐ray spectroscopy (EDX), elemental mapping, transmission electron microscopy (TEM), vibrating sample magnetometer (VSM) and thermal gravimetric analysis (TG). It was used as an efficient acidic nanomagnetic catalyst in the preparation of amidoalkyl phenols via multi‐component condensation of various amides (benzamide, acetamide and urea), phenolic compounds and aryl aldehydes or isatin under solvent‐free condition. High yield of products, easy work‐up and reusability of the catalyst can be mentioned as the advantages of described work.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Nanomagnetic Catalyst with Acetic Acid Tags: Application in the Synthesis of New Amidoalkyl Phenols under Solvent‐Free Condition

et al. 2019

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“…The common occurrence of nitrogen‐containing heterocycles in natural and synthetic drugs has motivated many efforts to synthesize pyrimidines, quinolines, and indolines exhibiting a wide range of essential biological functions. In particular, fused heterocycles such as pyranoquinolines, thienopyridines, and pyranopyrimidines have attracted considerable interest .…”

Section: Introductionmentioning

confidence: 99%

Preparation of Pyrido[2,3‐b]indole Derivatives Using Silicates of Group 1 and 2 Metals

Sheikh

Fazlinia

2018

Journal of Heterocyclic Chem

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An efficient synthesis of 2,4‐diaryl‐9H‐pyrido[2,3‐b] indole derivatives in aqueous medium via the three‐component reaction of indolin‐2‐one, a chalcone and ammonium acetate was developed using Na2SiO3, K2SiO3, Li2SiO3, CaSiO3, MgSiO3, BaSiO3, SrSiO3, and ZnSiO3 as catalysts. Results of activity evaluations indicated that among of the metal silicate used alkali metal silicates exhibits much higher activity than other samples due to the stronger basicity power and higher solubility in water. Under the optimum reaction conditions, all of the reactions with diverse aromatic aldehydes provided high yields in low reaction times.

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“…In fact, the synthetic methodologies to prepare 3,4‐disubstituted‐β‐naphthol are relatively rare in the literature . The multi‐functionalized sequential synthesis using simpler β‐naphthol as the substrates is a traditional method to prepare β‐naphthols with more elaborated skeletons . However, this method suffers from the length of synthetic steps and the lack of regioselectivity .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A

et al. 2018

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As equential synthesis of b-naphthols and naphtho [2,3-b]furan-2(3H)-ones (naphthofuranones) has been developed using ortho-alkynylarylketonesa st he substrates. The AgTFA-catalyzed ketonization generated the corresponding 1,5-diketonei ntermediates in situ;t hese weref urther cyclized via aldol condensation under basic conditions to obtain b-naphthol products in moderate to good yields. For the synthesis of naphtho[2,3-b]furan-2(3H)-ones, an additional lactonization step was appliedt og ive ab road range of products in good yields. Moreover,t his methodh as also been utilized in the synthesis of natural product negundin A.Scheme1.The reported methodsf or the synthesis of b-naphthols. Scheme2.Our methodology for the synthesis of5min KOH (10.0 equiv), MeOH, 85 8C, 3min < 59 [c] 585 8C, 5min LiOH (10.0equiv), MeOH, 85 8C, 1h < 58 [c] 685 8C, 5min KO t Bu (10.0 equiv), MeOH, rt, 1h < 34 [c] 785 8C, 5min KO t Bu (10.0 equiv), t-BuOH, rt, 1h < 42 [c] 885 8C, 5min KO t Bu (10.0 equiv), THF,rt, 1h -[d] 985 8C, 5min NaO t Bu (10.0 equiv), MeOH, rt, 1h < 51 [c] 10 H 2 O( 1.0 equiv), rt, 15 min KOH (10.0 equiv), MeOH,8 58C, 3min 61 11 H 2 O( 1.0 equiv), rt, 15 min KOH (10.0 equiv), MeOH,r t, 25 min 62 [a] Yields of isolated products are reported. [b] Only 1,5-diketone was observed.[ c] Product containedi mpurities. [d] Complex mixture. [e] O/N = overnight. Scheme3.Substrate scope.Y ields of isolated products are reported. [a] Only the 1,5-diketone was observed;[b] the reaction in step 1w as carried out at 85 8C. Scheme4.Substrate scope expansion. Yields of isolatedproducts are reported. [a] The reaction in step 1w as stirred at room temperature overnight; [b] the reaction in step 1 [b] was stirreda troomtemperaturef or 6h. Scheme5.Reactionmonitoring of compound 1z-OH. Scheme6.Scope of substrate for the synthesis of naphtho[2,3-b]furan-2(3H)ones. Yields of isolated products are reported.[a] The reaction in step 1was carried out at 85 8C. Scheme7.To tal synthesis of negundin A. 1 HNMR (400 MHz, CDCl 3 ): d = 7.66 (d, 1H, J = 8.4 Hz), 7.38-7.32 (m, 2H), 7.26-7.22 (m, 2H), 7.17-7.14 (m, 2H), 7.07-7.05 (m, 2H), 5.06

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Preparation of 1-amidoalkyl-2-naphthol derivatives using barium phosphate nano-powders

Cited by 51 publications

References 39 publications

Synthesis of Novel Nanomagnetic Catalyst with Acetic Acid Tags: Application in the Synthesis of New Amidoalkyl Phenols under Solvent‐Free Condition

Synthesis of Novel Nanomagnetic Catalyst with Acetic Acid Tags: Application in the Synthesis of New Amidoalkyl Phenols under Solvent‐Free Condition

Preparation of Pyrido[2,3‐b]indole Derivatives Using Silicates of Group 1 and 2 Metals

Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A

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