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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.


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Examples of useful transformations of 2,1-benzisoxazoles
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Sch1: Examples of useful transformations of 2,1-benzisoxazoles

Mentions: 2,1-Benzisoxazoles (anthranils) are important compounds, particularly as starting materials for the synthesis of 2-aminoarylketones [1–4]. A number of heterocyclic systems, such as quinolines, acridines, or quinazolines, can be synthesized either from the latter or, in some cases, directly from 1,2-benzisoxazoles [1–10] (Scheme 1). Of particular interest is the transformation of 3-aryl-2,1-benzisoxazoles into 2-aminobenzophenones, key intermediates in the synthesis of 1,4-benzodiazepines potent psychoactive drugs [11]. Patent literature discloses also a number of anthranils as key intermediates in the synthesis of various drugs, such as mycobacterial agents [12], farnesyl transferase inhibitors [13, 14], protein kinase inhibitors [15], and anticancer agents [16].


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)

Examples of useful transformations of 2,1-benzisoxazoles
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

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

Sch1: Examples of useful transformations of 2,1-benzisoxazoles
Mentions: 2,1-Benzisoxazoles (anthranils) are important compounds, particularly as starting materials for the synthesis of 2-aminoarylketones [1–4]. A number of heterocyclic systems, such as quinolines, acridines, or quinazolines, can be synthesized either from the latter or, in some cases, directly from 1,2-benzisoxazoles [1–10] (Scheme 1). Of particular interest is the transformation of 3-aryl-2,1-benzisoxazoles into 2-aminobenzophenones, key intermediates in the synthesis of 1,4-benzodiazepines potent psychoactive drugs [11]. Patent literature discloses also a number of anthranils as key intermediates in the synthesis of various drugs, such as mycobacterial agents [12], farnesyl transferase inhibitors [13, 14], protein kinase inhibitors [15], and anticancer agents [16].

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.


Related in: MedlinePlus