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General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

Wiȩcław M, Bobin M, Kwast A, Bujok R, Wróbel Z, Wojciechowski K - Mol. Divers. (2015)

Bottom Line: Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland.

ABSTRACT
Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.

No MeSH data available.


Formation of dihydroxylamine derivative 13
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Sch5: Formation of dihydroxylamine derivative 13

Mentions: According to the proposed mechanism, the formation of the intermediate nitroso compound 6 from the -adduct 4 is abandoned. More plausible seems the bis-silylation of the -adduct 4 to form the so-called “bis-silylated dihydroxylamine” 9. Compounds of this type were synthesized by the double deprotonation/silylation of some nitroalkenes [57–60]. The most fitting example is the formation of bis-silylated phenyldihydroxylamine 13 from 1-nitrocyclohexa-1,3-diene (12) (Scheme 5) [58].Scheme 5


General synthesis of 2,1-benzisoxazoles (anthranils) from nitroarenes and benzylic C-H acids in aprotic media promoted by combination of strong bases and silylating agents.

Wiȩcław M, Bobin M, Kwast A, Bujok R, Wróbel Z, Wojciechowski K - Mol. Divers. (2015)

Formation of dihydroxylamine derivative 13
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4591207&req=5

Sch5: Formation of dihydroxylamine derivative 13
Mentions: According to the proposed mechanism, the formation of the intermediate nitroso compound 6 from the -adduct 4 is abandoned. More plausible seems the bis-silylation of the -adduct 4 to form the so-called “bis-silylated dihydroxylamine” 9. Compounds of this type were synthesized by the double deprotonation/silylation of some nitroalkenes [57–60]. The most fitting example is the formation of bis-silylated phenyldihydroxylamine 13 from 1-nitrocyclohexa-1,3-diene (12) (Scheme 5) [58].Scheme 5

Bottom Line: Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.

View Article: PubMed Central - PubMed

Affiliation: Institute of Organic Chemistry, Polish Academy of Sciences, Ul. Kasprzaka 44/52, PO Box 58, 01-224, Warszawa, Poland.

ABSTRACT
Carbanions of phenylacetonitriles, benzyl sulfones, and dialkyl benzylphosphonates add nitroarenes at the ortho-position to the nitro group to form [Formula: see text]-adducts that, upon treatment with trialkylchlorosilane and additional base (t-BuOK or DBU), transform into 3-aryl-2,1-benzisoxazoles in moderate-to-good yields.

No MeSH data available.