IODINE CATALYZED CASCADE SYNTHESIS OF FLAVONE DERIVATIVES FROM 2'-ALLYLOXY-&amp;#945;, &amp;#946;-DIBROMOCHALCONES

Nawghare, Beena R.; Gaikwad, Sunil; Raheem, Abdul; Lokhande, Pradeep D.

doi:10.4067/s0717-97072014000100009

Cited by 13 publications

(10 citation statements)

References 4 publications

(4 reference statements)

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“…Therefore, in the first set of reactions, several substituted THβC (3a-3f) were evaluated, and it was found that the substrates which hold O-allyl group at meta position of phenyl ring afforded 6c in 65-70% yields. Next, we investigated the substrates 3g, 3h, 3i, and 3j ( Further, we extended our investigation toward the selective deallylation followed by dehydrogenation of Oallyl THβC; As per our previous report [19,20] , we have found that deallylation proceed by using molecular iodine in DMSO+H + (20 mol %) at 60 C and optimized condition in our hand (Table 1, entry 11). Thereafter, we have applied our previously developed protocol molecular iodine in DMSO/H + with 50 and 100 mol% at 90 C; it was observed that the aromatization of O-allyl-tetrahydoβ-carboline 3a, 3b, and 3g (Table 2, entry 11, 12) gave 4a, 5a with 75-80% yield with deallylation (Table 2, entry 11,12).…”

Section: Resultsmentioning

confidence: 79%

“…[19] The substoichiometric amount of I 2, in DMSO has been used for the cascade synthesis of flavones. [20] The iodine in DMSO at 130 C, it prefers deprotection of allyl group carboxylic ester [21] and direct C-deallylation of allyl group from the active methylene position [13] along with chemoselective oxidative dehydrogenation of allyloxy substituted β-anilinodihydro-chalcones to β-anilino-chalcones [22] was preferred reaction over deallylation (Figure 2). The Significant biological properties of βcarboline makes it synthetically important Unit.…”

Section: Introductionmentioning

confidence: 99%

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Iodine‐DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro‐β‐carboline

Gaikwad

Lokhande

2021

Journal of Heterocyclic Chem

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We have developed a simple method for the chemoselective aromatization of tetrahydro-β-carboline with selective nondeallylation O-allyl groups in the presence of iodine (100 mol %) in dimethyl sulfoxide/H 2 O 2 . A convergent approach toward the oxidative aromatization with selective deallylation (deprotection) of O-allyl-tetrahydro-β-carboline using iodine in dimethyl sulfoxide/HCl has been described. The present protocol contains cheap catalyst, easy work up, normal reaction conditions, and high selectivity.

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Section: Resultsmentioning

confidence: 79%

Section: Introductionmentioning

confidence: 99%

Iodine‐DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro‐β‐carboline

Gaikwad

Lokhande

2021

Journal of Heterocyclic Chem

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“…The use of iodine in the dimethylsulfoxide reagent to produce 2'-allyloxy-, -dibromochalcones (5), which lead to the equivalent 3-bromoflavones (6). When 2'-allyloxy chalcones were treated with DMSO-I2 reagent, the allyl group was removed easily, followed by cyclization and dehydrogenation, yielding flavones (7) [10].…”

Section: From 2'-allyloxy-α β-Dibromochalconesmentioning

confidence: 99%

Flavones and Their Derivatives: Synthetic and Pharmacological Importance

MOTGHARE¹,

KATOLKAR²,

CHACHERKAR³

et al. 2022

Asian J Pharm Clin Res

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Flavones (from the Latin flavus, which means “yellow”) are a kind of flavonoid with a backbone of 2-phenylchromen-4-one. Flavones, one of the most important classes of plant secondary metabolites, are well-known for their anti-cancer, anti-inflammatory, anti-microbial, antioxidant, anti-osteoporatic, anti-diabetic, anti-estrogenic, anti-allergic, and metal chelating properties. These family compounds have been intensively studied synthetically due to their wide spectrum of biological actions, and more than 4000 chemically distinct flavonoids have been identified from plants. However, new advances in synthetic chemistry have resulted in the production of a number of therapeutically important derivatives. This article summarizes the synthesis of flavones, their derivatives, and other flavone analogues which have the potential for treating a range of illnesses and ailments.

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“…1) (1)(2)(3). Although both glycosides are naturally occurring in the families of Rutaceae, Lamiaceae, Apiaceae, Scrophulariaceae (S. nadosa) (2)(3)(4)(5)(6)(7)(8)(9)(10), the industrial sector uses semisynthetic diosmin derived from hesperidin by a suitable oxidation reaction (I 2 /pyridine, I 2 /dimethylsulfoxide or other) (1)(2)(3)11,(15)(16)(17)(18). Hesperidin is most commonly isolated from dry orange or citrus peels (Citrus sinesis, L., Citrus aurantium, L., Citrus lemon, L., and other Citrus species) (3,8,10).…”

Section: Structure Sources and Isolationmentioning

confidence: 99%

Biopharmaceutical and marketing evaluation of diosmin- and hesperidin-containing products on the Bulgarian market

Ivanova

Hyusein

Slavov

et al. 2019

Scripta Scientifica Pharmaceutica

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INTRODUCTION: Diosmin and hesperidin are commonly used flavonoids in the therapy of vascular diseases. AIM: This study aimed to present an independent evaluation of the market status, quality and biopharmaceutical characteristics of diosmin-and hesperidin-containing oral tablet-products (DHCPs) on the Bulgarian market. MATERIALS AND METHODS: Seven products, among which medicines (used as reference) and food supplements, with sustainable or growing market were selected for the survey: Detralex 500 mg, Phlebodia 600 mg, Dioket 600 mg, Novarix 650 mg, Asketon 500 mg, Venocode and Dih max 1000 mg. Sales analysis for 2016, 2017 and 2018 (year-to-date) was done with the kind support of Iqvia TM. All products were subjected to European Pharmacopoeia (EP) tests for tablet quality-disintegration, resistance to crushing, uniformity of mass and uniformity of dosage units. Biopharmaceutical profile regarding tablet drug release and dissolution potency was investigated on EP Apparatus 2 (Paddle method). RESULTS: Although all products were found to almost fully fulfill the EP criteria, extremely unsatisfying drug release was established in all tested media (pH 1,5, pH 4,5 and pH 7,2), reaching not more than 1.6% of the labeled content after 24 hours for the best performing products-Novarix and Venocode. CONCLUSION: These results were not surprising considering diosmin and hesperidin's water insolubility and respective low bioavailability. However, it would be reasonable to approach these two bioactive compounds technologically in preformulation stage in order to improve their solubility and therapeutic potency.

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IODINE CATALYZED CASCADE SYNTHESIS OF FLAVONE DERIVATIVES FROM 2'-ALLYLOXY-α, β-DIBROMOCHALCONES

Cited by 13 publications

References 4 publications

Iodine‐DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro‐β‐carboline

Iodine‐DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro‐β‐carboline

Flavones and Their Derivatives: Synthetic and Pharmacological Importance

Biopharmaceutical and marketing evaluation of diosmin- and hesperidin-containing products on the Bulgarian market

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