Transition metals catalyzed C–C and C–O bonds formation: facile synthesis of flavans and benzoxepines

Ramulu, Bokka Venkat; Mahendar, Lodi; Krishna, Jonnada; Reddy, Alavala Gopi Krishna; Suchand, Basuli; Satyanarayana, Gedu

doi:10.1016/j.tet.2013.05.046

Cited by 19 publications

(7 citation statements)

References 71 publications

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“…50 and the three-step strategy for the synthesis of functionalized avans using combination of Pd and Cu catalysts. 51,52 These approaches are plagued with longer reaction times, multistep synthesis, and harsh reaction conditions, making them less attractive. In this context, signicantly enough, the ruthenium (1-3)b complexes catalyzed the reaction of 1-phenylethanol with 2-bromobenzyl alcohol to give the corresponding dehydrogenative alcohol-alcohol cross coupled product, which upon subsequent treatment with CuI yielded the desire avan product, 2-phenylchroman ( 16), in ca.…”

Section: Hydrogenation Of Olens and Ketonesmentioning

confidence: 99%

One pot tandem dehydrogenative cross-coupling of primary and secondary alcohols by ruthenium amido-functionalized 1,2,4-triazole derived N-heterocyclic carbene complexes

Kumar

Nettem

et al. 2022

RSC Adv.

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Section: Hydrogenation Of Olens and Ketonesmentioning

confidence: 99%

One pot tandem dehydrogenative cross-coupling of primary and secondary alcohols by ruthenium amido-functionalized 1,2,4-triazole derived N-heterocyclic carbene complexes

Kumar

Nettem

et al. 2022

RSC Adv.

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“…Ramulu et al in 2013 synthesized functionalized benzoxepines and also flavans via intermolecular palladium‐catalyzed C–C coupling and an intramolecular copper‐catalyzed C–O bond formation (SCHEME 2). [ 50 ] This strategy is a simple and practical method for the synthesis of benzoxepines and flavans compared with some of the previously reported methods.…”

Section: Palladium‐catalyzed Synthesis Of Oxepine Derivativesmentioning

confidence: 99%

Exciting progress in the transition metal‐catalyzed synthesis of oxepines, benzoxepines, dibenzoxepines, and other derivatives

Rafiee

Hasani

2021

Applied Organom Chemis

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From the past decade so far, the synthesis of seven‐membered oxacycles especially natural monocyclic oxepines and their annulated derivatives has received considerable attention. Due to the importance of these valuable scaffolds in natural products, pharmaceuticals, and prospective drugs, as well as their strong potential for use in the biosynthesis and metabolism of monocyclic and polycyclic aromatic compounds, a variety of synthesis strategies have been proposed to afford oxepine moiety. Among the versatile and attractive approaches, this review article focuses on the exciting developments in transition metal‐mediated reactions as the key step in the synthesis of oxepine derivatives from 2010 to early 2021.

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“…[93][94][95][96] This review focuses and precisely summarizes the methods established for the past 5 years, on the synthesis of flavans, neoflavans, and isoflavans. [41,[97][98][99][100] 2 | RESULTS AND DISCUSSION…”

Section: Introductionmentioning

confidence: 99%

Recent advances on the synthesis of flavans, isoflavans, and neoflavans

Sreenivasulu

Dakoju

Satyanarayana

2020

Journal of Heterocyclic Chem

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Heterocyclic compounds are the omnipresent structural cores comprising many natural and pharmaceutical products of biological significance. Significantly, heterocyclic compounds are widely distributed in nature, and also have applications in agrochemicals, sanitizers, as dyestuff, as copolymers, etc. Among heterocyles, flavonoids are a class of compounds that are highly interesting and constitute many natural products. In general, all flavanoids contains a basic core of C6‐C3‐C6 of phenyl‐benzopyran backbone. The relative placement of the phenyl group on to the benzopyran core makes further classification into flavanoids, isoflavanoids and neoflavanoids. Flavans (2‐aryl chroman) are subclass of anthoxanthanes exhibits a broad spectrum of biological properties such as anti‐inflammatory, anti‐oxidant, and anti‐malarial properties. Some representative naturally occurring products possessing flavan core are apigenin, luteolin, tangeretin, scutellarein, etc. On the other hand, some of the notable isoflavan‐based natural products are glabridin and (S)‐(−)‐equol. Glabridin is isolated from Licorice roots, which regulates paraoxonase (PON2) levels. While the simple isoflavan (S)‐(−)‐equol, is produced from soy isoflavone intake. Also, natural products such as dalbergichromene, centchroman, and (+)‐myristinin A possess neoflavan (4‐aryl‐3,4‐dihydro‐2H‐chromenes) core structure. Owing to their broad biological and pharmacological properties, synthetic chemists are fascinated in developing new routes toward their synthesis. As a result, a decent number of reports have been established in the literature. Thus, for the past 5 years of time frame, many new methodologies have been witnessed, for the synthesis of various flavan systems. This review emphasizes most of the significant methods on accomplishing flavans, isoflavans and neoflavans and also focused on their applications to the synthesis of relevant natural as well as biologically active products.

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Transition metals catalyzed C–C and C–O bonds formation: facile synthesis of flavans and benzoxepines

Cited by 19 publications

References 71 publications

One pot tandem dehydrogenative cross-coupling of primary and secondary alcohols by ruthenium amido-functionalized 1,2,4-triazole derived N-heterocyclic carbene complexes

One pot tandem dehydrogenative cross-coupling of primary and secondary alcohols by ruthenium amido-functionalized 1,2,4-triazole derived N-heterocyclic carbene complexes

Exciting progress in the transition metal‐catalyzed synthesis of oxepines, benzoxepines, dibenzoxepines, and other derivatives

Recent advances on the synthesis of flavans, isoflavans, and neoflavans

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