An Improved Method for the Synthesis of Cyclopropyl Ketoesters

Lokanatha, K. M.; Anjanamurthy, C.; Radhakrishna, P.

doi:10.1080/00397919008052837

Cited by 13 publications

(6 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Chalcones 13a-c were prepared in excellent yields by Claisen condensation reaction of 4 1 -methylthio acetophenone 11 with benzaldehydes 12a-c in the presence of sodium hydroxide in water-ethanol mixture [9]. Cyclopropyl keto esters 14a-c were prepared in good yields by the reaction of chalcones 13a-c with ethyl chloro acetate in the presence of powdered sodium in dry benzene [7,3]. The structures of the compounds were based on IR, 1 H NMR, Mass spectra and elemental analysis data.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis of new tetralone ester intermediates for podophyllotoxin analogues

Raju¹,

Basavaraju²

2013

pacs

View full text Add to dashboard Cite

Podophyllotoxin is a naturally occurring lignan compound which exhibits anticancer, anti AIDS and other biological activities. New tetralone ester intermediates of podophyllotoxin analogues were synthesised in very good yields by chalcone route. They were synthesized by replacing the 3,4,5-trimethoxy groups in podophyllotoxin respectively with hydrogen, methoxy and nitro group and also 1,3methylene dioxy group with methyl thio group to study structure activity relationship. All the products were characterized by spectral and elemental analysis data.

show abstract

Section: Chemistrymentioning

confidence: 99%

Synthesis of new tetralone ester intermediates for podophyllotoxin analogues

Raju¹,

Basavaraju²

2013

pacs

View full text Add to dashboard Cite

show abstract

“…The cyclopropyl keto esters (8a-d) were prepared in good yields by the reaction of chalcones (7a-d) with ethyl monochloro acetate in the presence of powdered sodium in dry benzene [19]. The IR spectra showed stretching frequencies at 1593-1598, 1674-1678 and 1735-1741 cm -1 for C=C, C=O and ester C=O of cyclopropyl keto esters respectively.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and study of antimicrobial activity of new tetralone esters

et al. 2014

View full text Add to dashboard Cite

“…They were recrystallized from methanol (Scheme 1). (2) with benzaldehydes (3a,b) separately in the presence of sodium hydroxide in ethanol-water mixture [5,6]. The cyclopropyl ketones (5a,b) were prepared in high yields by the reaction of chalcones (4a,b) with trimethyl sulphoxonium iodide in presence of sodium hydride in dry benzene [7][8][9].…”

Section: General Procedures For the Synthesis Of Tetralones (6 7)mentioning

confidence: 99%

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

2016

View full text Add to dashboard Cite

Podophyllotoxin has captured the attention of chemists all over the world for its biological activity. It was isolated from many plants of Podophyllum species such as Podophyllum emodi, Podophyllum peltatum and others. It mainly exhibits anticancer, antimitotic, antimalarial, anti-aids and other activities. Its use is restricted due to its toxicity and unfavourable solubility. It was aimed to synthesize some new heterocyclic analogues of podophyllotoxin by changing the substituents by changing lactone ring with pyrazoline ring and substituents in ring C with hydrogen and methoxy group. Chalcones were prepared by Claisen-Schmidt reaction of 1,3-methylene dioxyacetophenone with benzaldehyde and p-anisaldehyde. The reaction of chalcone with trimethylsulphoxonium iodide in presence of sodium hydride gave cyclopropyl ketone. Intramolecular cyclization reaction of cyclopropyl ketone gave tetralone intermediates of podophyllotoxin. They are obtained in good yields. The structure of all the products was confirmed by spectral data.

show abstract

An Improved Method for the Synthesis of Cyclopropyl Ketoesters

Cited by 13 publications

References 3 publications

Synthesis of new tetralone ester intermediates for podophyllotoxin analogues

Synthesis of new tetralone ester intermediates for podophyllotoxin analogues

Synthesis and study of antimicrobial activity of new tetralone esters

Synthesis and characterization of tetralones as intermediates for podophyllotoxin analogues

Contact Info

Product

Resources

About