21733-37-9Relevant academic research and scientific papers
Novel results from the sodium borohydride reduction of E-3-benzylidene- chromanone epoxides in methanol: Formation of an interesting class of chromanone-derived methoxydiols
Mandal, Tapas K.,Sepay, Nayim,Chatterjee, Nachiketa,Mallik, Asok K.
, p. 1805 - 1813 (2014/01/17)
Sodium borohydride reduction of a number of E-3-benzylidenechromanone epoxides in methanol gave an interesting class of methoxydiols characterized as 3(S*),4(S*)-dihydroxy-3-[α(R*)-methoxybenzyl]chromans, along with the corresponding cis-epoxyalcohols. Mechanistic pathway for the formation of the new type of methoxydiols has been suggested to be methoxide-induced opening of the epoxide ring of an intermediate related to the trans-epoxyalcohols. Sodium borohydride reduction of E-2-benzylidene-1-tetralone epoxide also gave similar results.
Highly enantioselective epoxidation of multisubstituted enones catalyzed by non-heme iron catalysts
Wang, Bin,Wang, Shoufeng,Xia, Chungu,Sun, Wei
supporting information; experimental part, p. 7332 - 7335 (2012/09/22)
Iron(II) efficiency: The iron complexes of N4 ligands, derived from proline and benzimidazole, exhibited an unprecedented activity and enantioselectivity for the epoxidation of a variety of di- and trisubstituted enones (see scheme). This syste
Synthesis of novel tricyclic heterocyclic compounds as potential anticancer agents using chromanone and thiochromanone as synthons
Hammam, Abou El-Fotooh G.,Fahmy,Amr, Abdel-Galil E.,Mohamed, Ashraf M.
, p. 1985 - 1993 (2007/10/03)
The arylmethylene of benzopyrane or benzothiopyrane 3,4 have been synthesized and condensed with hydrazine, guanidine and thiourea to yield pyrazole 5-8, aminopyrimidine 9,10 and thioxopyrimidine derivatives 11,12, respectively. Compounds 3 or 4 on treatment with malononitrile in the presence of ammonium acetate/acetic acid or in the presence of piperidine/ methanol to yield benzopyrano- and benzothiopyranopyridine 13,14 and benzopyrano- and benzothiopyrane 15,16, respectively. The oxirane of compound 3 is prepared and condensed with CS2 to yield the tricyclic system, thioxothienobenzopyrane 21. Ylidenemalononitrile for the ketone 1 and 2 are synthesized and condensed with aromatic aldehyde in presence of ammonium acetate/acetic acid to yield benzopyranopyridine and benzothiopyranopyridine derivatives 24,25, respectively, which are the isomer of compounds 13,14. Ylidenemalononitrile on condensation with phenylisothiocyanate yields benzo-pyrano- and benzothiopyranothioxopyridine 28,29, respectively.
Dimethyldioxirane Oxidation of 3-Arylidenechromanones
Adam, Waldemar,Halasz, Judit,Levai, Albert,Nemes, Csaba,Patonay, Tamas,Toth, Gabor
, p. 795 - 804 (2007/10/02)
Oxidation of the (E) and (Z) isomers of the 3-arylidenechromanones 5 by isolated dimethyldioxirane (as acetone solution) at ambient temperature resulted in the formation of the spiro epoxides trans- and cis-6, respectively, in moderate yields (23-51percent), together with considerable amounts (16-40percent) of the 3-aroylchromones 7 from both (E)- and (Z)-5 isomers.Minor products, namely 3-(α-hydroxy-4-methoxy-benzyl)-4H-1-benzopyran-4-one (8b), 1a,7a-dihydro-7a-(α-hydroxy-4-methylbenzyl)-7H-oxirenobenzopyran-7-one (9d), and the 1a,7a-dihydro-7a-aroyl-7H-oxirenobenzopyran-4-ones 10a-c have also been isolated and characterized.Presumably, the formation of 3-aroylchromones 7 can be attributed to competitive allylic oxidation with dimethyldioxirane to afford first the 3-(α-hydroxyarylmethyl)chromones 8, whose secondary alcohol functionality is subsequently oxidized by dimethyldioxirane to give the 3-aroylchromones 7.Further oxidation of the latter by dioxirane affords the epoxides 10, as established by a control experiment.Alternatively, first oxidation of 8 to yield epoxide 9 and subsequent oxidation of the alcohol functionality to afford the overoxidized product 10 cannot be disposed of on grounds of our product data.Nonetheless, despite the moderate yields of the desirable chromanone epoxides 6, the stereoselective oxidation directly of the chromanones by dimethyldioxirane offers a convenient preparation.Relative configuration and stereochemistry of compounds 6-10 were elucidated by NMR spectroscopy and AM1 calculations. - Key Words: Chromanones / Dimethyldioxirane / Epoxides
Antifertility Agents: Part XLIII - Synthesis of 3-Aryl-4,5-dihydro-2-substituted-5-tosyl-2H-pyrazoloquinolines and 2,4-Dihydro-3-phenylbenzopyranopyrazoles and Their Derivatives
Sangwan, Naresh K.,Kelkar, Prabhakar M.,Rastogi, Shri Nivas,Anand, N.
, p. 639 - 644 (2007/10/02)
2,3-Dihydro-1-tosyl-4(1H)-quinolones (5-7) on formylation give the corresponding 3-hydroxymethylene derivatives (11-13) of which 12 and 13 react with piperazine to afford N,N-bis-substituted piperazines (15 and 16).Refluxing of 11-13 with substituted hydr
