Limits...
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.


Proposed mechanism for the formation of anthranil and acridine in reactions of -adduct 4 with trimethylchlorosilane
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4591207&req=5

Sch4: Proposed mechanism for the formation of anthranil and acridine in reactions of -adduct 4 with trimethylchlorosilane

Mentions: Analysis of the results presented in Table 1 led us to propose another mechanistic pathway leading to acridines and anthranils (Scheme 4).Scheme 4


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)

Proposed mechanism for the formation of anthranil and acridine in reactions of -adduct 4 with trimethylchlorosilane
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch4: Proposed mechanism for the formation of anthranil and acridine in reactions of -adduct 4 with trimethylchlorosilane
Mentions: Analysis of the results presented in Table 1 led us to propose another mechanistic pathway leading to acridines and anthranils (Scheme 4).Scheme 4

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.