A facile synthesis of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones and naphthoxazin-2-ones and their reactions with organolithium and Grignard reagents -: Preparation of N-[1-(2′-hydroxyphenyl)alkyl]amides

被引：29

作者：

Cimarelli, C ^{[1
]}

Palmieri, G ^{[1
]}

Volpini, E ^{[1
]}

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

来源：

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 2004年 / 82卷 / 08期

关键词：

benzoxazinones; naphthoxazinones; organometallic reagents; amide preparation; aminoalkylphenols;

D O I：

10.1139/V04-100

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A facile and simple method for the preparation of 3,4-dialkyl-3,4-dihydro-2H-1,3-benzoxazin-2-ones or naphthoxazin-2-ones in high yields from aminoalkylphenols and aminoalkylnaphthols is described. The reactions of the products obtained with organolithium and Grignard reagents were studied, and a method for the preparation of N-[1-(2-hydroxyphenyl)alkyl]-N-alkylamides, which are of pharmaceutical interest, from benzoxazinones was developed. A possible reaction mechanism is also proposed. The relative configuration of chiral products was determined from conformational analysis of H-1 NMR spectra.

引用

页码：1314 / 1321

页数：8

共 36 条

[1] POTENTIAL ANTIMALARIALS .21. MANNICH BASE DERIVATIVES OF 4-[7-CHLORO(AND 7-TRIFLUOROMETHYL)QUINOLIN-4-YLAMINO]PHENOLS [J].

BARLIN, GB ;

IRELAND, SJ ;

NGUYEN, TMT ;

KOTECKA, B ;

RIECKMANN, KH .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (08) :1553-1560

[2]

BARLIN GB, 1994, AUST J CHEM, V47, P1143

[3] LIGAND-ACCELERATED CATALYSIS [J].

BERRISFORD, DJ ;

BOLM, C ;

SHARPLESS, KB .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (10) :1059-1070

[4] Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes [J].

Cardellicchio, C ;

Ciccarella, G ;

Naso, F ;

Perna, F ;

Tortorella, P .

TETRAHEDRON, 1999, 55 (51) :14685-14692

[5] A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

TETRAHEDRON-ASYMMETRY, 2002, 13 (22) :2417-2426

[6] Stereoselective alkylation of chiral 2-imidoylphenols with organolithium reagents: Synthesis of enantiopure 2-aminoalkylphenols [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04) :1200-1206

[7] Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: Stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation [J].

Cimarelli, C ;

Mazzanti, A ;

Palmieri, G ;

Volpini, E .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (14) :4759-4765

[8] Reduction of 4H-chromen-4-ylidene amines:: synthesis of 2-[(1-aminoalkyl)-3-aryl-2-propenyl] phenols [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

TETRAHEDRON, 2001, 57 (31) :6809-6814

[9] Ready N-alkylation of enantiopure aminophenols:: synthesis of tertiary aminophenols [J].

Cimarelli, C ;

Palmieri, G ;

Volpini, E .

TETRAHEDRON, 2001, 57 (28) :6089-6096

[10] Diels-Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives [J].

Consonni, R ;

Croce, PD ;

Ferraccioli, R ;

LaRosa, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (15) :1809-1814

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