ChemInform Abstract: A Green and Selective Synthesis of 2‐Aryloxazines and 2‐Aryltetrahydropyrimidines.

Mohammadpoor‐Baltork, Iraj; Tangestaninejad, Shahram; Mirkhani, Valiollah; Eskandari, Zohre

doi:10.1002/chin.201132025

Cited by 8 publications

(9 citation statements)

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“…with aldehydes (1 eq.) [7][8][9][10][11][12][13][14][15][16] . Some catalysts have been applied for this reaction, such as silica chloride 7 , H 3 PW 12 O 40 supported MCM-41 8 , cyanuric chloride 9 , 1-butyl-3-methylimidazolium trifluoroacetate 10 , PPA-SiO 2 11 , DABCO-bromine 12 , TMSCl 13 , silica-supported H 14 [NaP 5 W 30 O 110 ] nanoparticles 14 , SbCl 3 /SiO 2 15 and ZrO(OTf) 2…”

Section: Introductionmentioning

confidence: 99%

“…and aldehydes (1 eq.) using some catalysts, e. g. ZrO(OTf) 2 16 , selectfluor TM 24 and TaCl 5 25 . Nevertheless, most of the reported methods for the synthesis of the xanthenes derivatives are associated with one or more of the following drawbacks: (i) moderate yields, (ii) long reaction times, (iii) the use of large amount of catalyst, and (iv) the use of expensive, non-available or toxic catalysts, and (v) no agreement with the green chemistry protocols.…”

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confidence: 99%

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Solvent-Free Synthesis of 1,8-Dioxo-octahydroxanthenes and 14-Aryl-14H-dibenzo[a,j]xanthenes using Saccharin Sulfonic Acid as an Efficient and Green Catalyst

Zare

Mokhlesi

Hasaninejad

et al. 2012

E-Journal of Chemistry

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Saccharin sulfonic acid (SaSA) is utilized as a highly efficient, green and inexpensive sulfonic acid-containing catalyst for the following one-pot multi-component organic transformations: (i) the condensation of dimedone (2 eq.) with aromatic aldehydes (1 eq.) leading to 1,8-dioxo-octahydroxanthenes, and (ii) the reaction of 2-naphthol (2 eq.) with arylaldehydes (1 eq.) leading to 14-aryl-14H-dibenzo[a,j]xanthenes. In these protocols, the title compounds are produced in high to excellent yields and in relatively short reaction times under solvent-free conditions.

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Section: Introductionmentioning

confidence: 99%

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confidence: 99%

Solvent-Free Synthesis of 1,8-Dioxo-octahydroxanthenes and 14-Aryl-14H-dibenzo[a,j]xanthenes using Saccharin Sulfonic Acid as an Efficient and Green Catalyst

Zare

Mokhlesi

Hasaninejad

et al. 2012

E-Journal of Chemistry

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“…Literature survey shows a number of routes to obtain 1,8-dioxooctahydroxanthene and its variants, employing either different starting materials or catalysts. Literature methods include catalysts like molecular iodine [18], zirconyl triflate [19], nano-TiO2 [20], nanoparticles of iron(II, III) oxide [21], iron(III) complex [22], nano-SPA [23] and barium perchlorate [24] among others. However, contemporary research in organic chemistry desires protocols to be in conformity with green chemistry principles.…”

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confidence: 99%

Efficient and Clean Synthesis of 1,8-Dioxooctahydroxanthenes in Aqueous Medium

Pore¹

2018

Asian J. Chem.

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INTRODUCTION Xanthenes have attracted a number of research efforts in synthetic organic chemistry due to their wide range of biological and pharmacological properties like antiviral [1], antibacterial [2] and anti-inflammatory activities [3], as well as in photodynamic therapy [4] and as antagonists of the paralyzing action of zoxazolamine [5]. Xanthenes are also available from many natural sources. The prominent among them are dibenzoxanthenes, hexahydroxanthene and octahydroxanthene. Xanthenes are frequently occurring motifs in a number of natural products [6] and have been used as versatile synthons due to the inherent reactivity of inbuilt pyran ring [7]. Octahydroxanthene derivatives containing a structural unit of benzopyrans can be used as antispasm agents [8] and fluorescent fuel [9]. Furthermore, due to their useful spectroscopic properties, they are used as dyes and pigments [10,11], in laser technologies [12] and in fluorescent materials for visualization of biomolecules [13]. Xanthenes are also known to possess many pharmacological properties. Allanxanthone C, a xanthene derivative obtained from Allanblackia monticola exhibits excellent biological properties [14]. Ehretianone, a quinonoid xanthene obtained from Ehretia buxifolia is reported to possess anti-snake venom activity [15]. A spiro-compound of xanthene, xanthene spiropiperidine, is well-known as a sedative and antihistaminic agent

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“…Mohammadpoor-Baltork et al demonstrated that 2,4-disubstituted quinolines (Scheme 10.77) can easily be prepared in an one-pot reaction of structurally diverse 2-aminoaryl ketones with various arylacetylenes in the presence of K 5 CoW 12 O 40 · 3H 2 O as a reusable and environmentally benign catalyst under solvent-free MW irradiation conditions[186]. A solvent-free MW-assisted method was described byGarella et al for the synthesis of substituted quinoline derivatives via Friedlander cyclization, employing a reusable solid catalyst (silica-propylsulfonic acid) [187].…”

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confidence: 99%