Homoisoflavanones from Lespedeza juncea

Tantray, Mudasir Ahmad; Shawl, A. S.; Khuroo, Mohammad Akbar; Ali, Naji M.

doi:10.1007/s10600-008-9091-2

Cited by 4 publications

(1 citation statement)

References 10 publications

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“…Thus the presented work disclosed a new protocol for unification of harmol and benzothizoline in order to bring existence of their hybrid molecules with expected new and strong biological profile. Therefore in continuation of our quest for unification of bioactive molecules lead to structurally diverse molecular hybrids via development of simple and efficient protocols . Herein we developed a novel, efficient and metal free synthesis of harmol assisted benzothiazoline hybrids from synthesized harmol adduct and 2‐aminothiophenol (5 mmol) each using ultra sonication waves upto 11 h in PEG as solvent as well as catalyst at 35 °C (Scheme ).…”

Section: Introductionmentioning

confidence: 99%

Efficient Metal‐Free Process: A Facile Synthesis of Biologically Versatile Harmol‐Linked Benzothiazoline Hybrids

2020

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Highly efficient and eco‐pure methodology has been disclosed for the synthesis of biologically versatile harmol linked benzothiazoline hybrid molecules. The reactions were carried out using (5 mmol) of harmol adduct and (5 mmol) of 2‐aminothiophenol added in 10 ml of PEGs under sonication at 35 °C to obtain harmol linked benzothiazoline confirmed by spectral analysis. A library of hybrid molecules has been synthesized using variable 2‐aminothiophenols and 2‐bromoacetophenones. The reactions were completed in petite reaction time and the products were obtained in moderate to good yields. The reaction medium could be recycled and reused for more than five times without loss of its proficiency added the protocol a wide scope.

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Section: Introductionmentioning

confidence: 99%

Efficient Metal‐Free Process: A Facile Synthesis of Biologically Versatile Harmol‐Linked Benzothiazoline Hybrids

2020

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Diastereodivergent Synthesis of Syn‐ and Anti‐9‐Hydroxyhomoisoflavanone and its Application to the Total Syntheses of (±)‐Homoferrugenone and (±)‐Portulacanone F

et al. 2022

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The diastereodivergent synthesis of synand anti-9-hydroxyhomoisoflavanone from various chromones and carbaldehydes is described. The synthetic approaches involving the reductive aldol reaction or the Morita-Baylis-Hillman reaction followed by syn-selective 1,4-reduction provide both diastereomers of β-hydroxy chroman-4-ones in 51-98% yield with anti (2 : 1-16 : 1 anti/syn) or 22-80% yield with syn (5 : 1-48 : 1 syn/anti) diastereoselectivity. The ambiguity surrounding the stereochemistry of two 9-hydroxyhomoisoflavanones, homoferrugenone and portulacanone F was elucidated via the first total syntheses.

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