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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 anthranils from nitroarenes and phenylacetonitriles in protic media
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Sch3: Formation of anthranils from nitroarenes and phenylacetonitriles in protic media

Mentions: The latter method, although limited to the synthesis of 2-aryl-substituted 2,1-benzisoxazoles, seems to be the most versatile one giving access to the variously substituted 3-aryl-2,1-benzisoxazoles [32]. The whole reaction consists of several reversible steps, and its mechanism is shown in Scheme 3.


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 anthranils from nitroarenes and phenylacetonitriles in protic media
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch3: Formation of anthranils from nitroarenes and phenylacetonitriles in protic media
Mentions: The latter method, although limited to the synthesis of 2-aryl-substituted 2,1-benzisoxazoles, seems to be the most versatile one giving access to the variously substituted 3-aryl-2,1-benzisoxazoles [32]. The whole reaction consists of several reversible steps, and its mechanism is shown in Scheme 3.

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.