Regioselectivity of nitrilimines 1,3‐dipolar cycloaddition: Novel synthesis of spiro[4,4]nona‐2,8‐dien‐6‐one derivatives

Miqdad, Omar A.; Abunada, Nada M.; Hassaneen, Hamdi M.

doi:10.1002/hc.20666

Cited by 8 publications

(2 citation statements)

References 34 publications

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“…Compounds 2a-d were characterized and confirmed by comparison with literature data [18,19]. Compounds 3a, 3c, 3d, 3f, 3g, 3i, 3l, 3m, 3o, 3r, 3s and 3x [20][21][22][23][24][25][26][27][28] were prepared according to the general method and structures were confirmed via comparison with literature data. …”

Section: General Procedures For the Synthesis Of 4-arylidene-2-phenyl-mentioning

confidence: 99%

Potent Anticonvulsant 1H-Imidazol-5(4H)-One Derivatives with Low Neurotoxicity

Mohamed¹,

Mahmoud²,

Sayed³

et al. 2012

OJMC

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We report here the synthesis and in vivo anticonvulsant/neurotoxicity activities of a series of compounds belonging to 2-aryl-4-arylidene-1-phenyl-1H-imidazol-5(4H)-one. The scaffold is based on the commonality of 5-membered lactam ring structures as successful anticonvulsant agents. The present compounds exhibited a range of anticonvulsant activity in pentylenetetrazole (PTZ)-induced seizure test. In particular, the protection was excellent by compounds bearing furylmethylidene on C4, possibly due to good pharmacokinetic properties. It was found that high lipophilicity and/or electron deficient aryl ring substitution at C4 compromised the anticonvulsant activities. For example, chloro analogues were found much less active than unsubstituted phenyl or furyl derivatives. Regarding side effects, active compounds exerted no observable neurotoxic effect at their therapeutic doses in Chimney test.

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Section: General Procedures For the Synthesis Of 4-arylidene-2-phenyl-mentioning

confidence: 99%

Potent Anticonvulsant 1H-Imidazol-5(4H)-One Derivatives with Low Neurotoxicity

Mohamed¹,

Mahmoud²,

Sayed³

et al. 2012

OJMC

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“…Disubstituted alkenes are typically competent substrates, with trisubstituted olefins reacting more sluggishly [ 9 ]. Nitrile imines are also effectively applied in the cycloaddition reaction with exocyclic alkenes [ 10 ] to form spirocyclic products containing 4-substituted [ 11 ] or 5-substituted pyrazole/pyrazoline cycles [ 12 ]. However, it has been shown that generally intermolecular nitrile imine cycloadditions favors the formation of a regioisomer with the most sterically encumbered substituent of the dipolarophile in the 5-position of the resulting heterocycle [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Regioselective Cycloaddition of Nitrile Imines to 5-Methylidene-3-phenyl-hydantoin: Synthesis and DFT Calculations

Filkina

Baray

Белоглазкина

et al. 2023

IJMS

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Nitrile imine cycloaddition to hydantoins containing an exocyclic C=C double bond has been previously described in a very limited number of examples. In this work, regioselective synthesis of spiro-pyrazoline-imidazolidine-2,4-diones based on a 1,3-dipolar cycloaddition reaction of nitrile imines to 5-methylidene-3-phenyl-hydantoin have been proposed. It was found that, regardless of the nature of the aryl substituents at the terminal C and N atoms of the C-N-N fragment of nitrile imine (electron donor or electron acceptor), cycloaddition to the 5-methylidenhydantoin exocyclic C=C bond proceeds regioselectively, and the terminal nitrogen atom of the nitrile imine connects to the more sterically hindered carbon atom of the double bond, which leads to the formation of a 5-disubstituted pyrazoline ring. The observed cycloaddition regioselectivity was rationalized using DFT calculations of frontier molecular orbital interactions, global CDFT reactivity indices, and minimum energy paths.

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ChemInform Abstract: Regioselectivity of Nitrilimines 1,3‐Dipolar Cycloaddition: Novel Synthesis of Spiro[4,4]nona‐2,8‐dien‐6‐one Derivatives.

2011

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Regioselectivity of Nitrilimines 1,3-Dipolar Cycloaddition: Novel Synthesis of Spiro[4,4]nona-2,8-dien-6-one Derivatives. -1,3-Dipolar cycloaddition of nitrilimines generated in situ from corresponding hydrazonoyl halides such as (II) with 4-arylideneimidazolones (I) affords the title spiro-compounds (III) (13 examples) in high yields. -(MIQDAD, O. A.; ABUNADA*, N. M.; HASSANEEN, H. M.; Heteroat. Chem. 22 (2011) 2, 131-136, http://dx.

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Regioselectivity of nitrilimines 1,3‐dipolar cycloaddition: Novel synthesis of spiro[4,4]nona‐2,8‐dien‐6‐one derivatives

Abstract: Regioselective 1,3-dipolar cycloaddition of nitrilimines (generated in situ from dehydrohalogenation of the corresponding hydrazonoyl halides by the action of triethylamine)

Cited by 8 publications

References 34 publications

Potent Anticonvulsant 1H-Imidazol-5(4H)-One Derivatives with Low Neurotoxicity

Potent Anticonvulsant 1H-Imidazol-5(4H)-One Derivatives with Low Neurotoxicity

Regioselective Cycloaddition of Nitrile Imines to 5-Methylidene-3-phenyl-hydantoin: Synthesis and DFT Calculations

ChemInform Abstract: Regioselectivity of Nitrilimines 1,3‐Dipolar Cycloaddition: Novel Synthesis of Spiro[4,4]nona‐2,8‐dien‐6‐one Derivatives.

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