3'-(p-Nitrophenyl)-2-phenyl-4'-(p-tolyl)spiro[isoquinoline-3(2H),5'(4'H)-isoxazolin]-4(1H)-one

Rahima, Badri; Kerbal, Abdelali; Najib, Ben Larbi; El-Bali, Brahim; Escudié, J.; Ranaivonjatovo, H.; Bolte, Michael

doi:10.1107/s010827019909825x

Cited by 8 publications

(11 citation statements)

References 1 publication

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“…[25][26][27][28] We have observed this feature in the case of 3-méthoxycarbonyle-4H-1-benzopyran-4-one, 9 and of the 3-toluidene-2,3-dihydro-4(1H)-isoquinolone. 14,24 . The compounds 7-11 are highly sensitive to pH of solution; they decompose in the presence of traces of acids.…”

Section: 24mentioning

confidence: 99%

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Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

Houari¹,

Kerbal²,

Bennani³

et al. 2008

Arkivoc

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Five new 3',4'-substituted-spiro[isochromene-3,5'-isoxazolin]-4(1H)-ones 7-11 have been prepared in the reaction of p-R-benzadoxime 2-6 with 3-para-methoxy-benzylidene-isochroman-4-one 1. The reaction occurs by a 1,3-dipolar cycloaddition mechanism which leads to the regiospecific formation of various spiro-isoxazolines 7-11. It is concluded that rigid (O 1'group may be responsible for the biological activity observed in antitubercular test with these hyper inter-organised spiro-isoxazoline derivatives. However, subtle alteration by addition of a substituted aryl groups affecting the charge distribution of the terminal heteroatom O 1' confers significant improvements in biological effects.

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Section: 24mentioning

confidence: 99%

“…9 We also studied the regionand the stereochemistry of the reaction of diarylnitrilimines with the 2-arylidene-indan-1-ones, 10 3-arylidene-tetraline-4-ones, [11][12] 3-arylidene-isothiochroman-4-ones, 13 and lately the 3-toluidene-2,3-dihydro-4(1H)-isoquinolone, 14 where the dipolarophilic site is exocyclic.…”

Section: Chemistrymentioning

confidence: 99%

Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

Houari¹,

Kerbal²,

Bennani³

et al. 2008

Arkivoc

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“…9 We also studied the regio and stereochemistry of the reaction of diarylnitrilimines with the 2-arylidene-indan-1-ones, 10 3-arylidene-tetraline-4-ones, 11,12 3-arylidene-isothiochroman-4-ones 13 and recently the 3-toluidene-2,3-dihydro-4(1H)-isoquinolone with exocyclic dipolarophile groups. 14 In our ongoing program, we report an efficient and short synthesis of new spiroheterocycles in good yields from 1,3-dipolar cycloaddition of dipolarophiles with the appropriate p-R 2 -benzadoxime. The pharmacological investigations as antitubercular activity are also discussed.…”

Section: And Antibacterial Agents (Gram+ Andmentioning

confidence: 99%

Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H-spiro[isoquinoline-3,5'-isoxazol]-4-ones

Hadda¹,

Rahima²,

Kerbal³

et al. 2007

Arkivoc

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Synthesis of a series of fourteen novel 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'Hspiro[isoquinoline-3,5'-isoxazol]-4-ones was accomplished in good yield by regio and stereoselective 1,3-dipolar cycloaddition of p-R 2 -benzadoxime 4-8 with dipolarophiles (3Z)-3-The structure of the isolated products 9-23 was established through different spectroscopic techniques. X-Ray crystal structure analysis of one of the products confirms the structure and the selective region and stereochemistry of this cycloaddition. Their antitubercular activity is also evaluated.

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“…We also studied the regio-and the stereochemistry of the reaction of diaryl-nitrilimines with the 2-aryliden-indan-1-ones [10], 3-aryliden-tetraline-4-ones [11,12], 3-aryliden-isothiochroman-4-ones [13] and lately some isoquinolones [14], where the site of the dipolarophiles is exocyclic. In this work dipolarophiles 1-4 have been prepared by a simple condensation of a para-substituted-benzaldehydes with the isothiochroman-4-ones in an acidic environment [15].…”

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confidence: 99%

Synthesis of new spiro‐[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones

Bennani¹,

Baba²,

Larbi³

et al. 2007

Journal of Heterocyclic Chem

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A series of seven new 2′,3′,4′‐substituted spiro[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones (7‐13) has been prepared in the reaction of benzylidene(phenyl)azane oxide (5) or benzylidene(methyl)azane oxide (6) with (3Z)‐3‐(4‐substituted‐benzylidene)‐1H‐isothio‐ chromen‐4(3H)‐one (1‐4). The reaction occurs by a 1,3‐dipolar cycloaddition mechanism that leads to the regiospecific formation of various spiroisoxazolidines (7‐13).

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3'-(p-Nitrophenyl)-2-phenyl-4'-(p-tolyl)spiro[isoquinoline-3(2H),5'(4'H)-isoxazolin]-4(1H)-one

Cited by 8 publications

References 1 publication

Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

Drug design of new antitubercular agents: 1,3-dipolar cycloaddition reaction of arylnitriloxides and 3-para-methoxy-benzylidene-isochroman-4-ones

Looking for a new antitubercular pharmacophore site: synthesis and bioactivity of spiroheterocycles 2,3',4'-tri-subsituted-1,2-dihydro-4H,4'H-spiro[isoquinoline-3,5'-isoxazol]-4-ones

Synthesis of new spiro‐[isothiochromene‐3,5′‐isoxazolidin]‐4(1H)‐ones

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