A Direct Synthesis of Oxazoles from Aldehydes

被引：63

作者：

Graham, Thomas H. ^{[1
]}

机构：

[1] Merck & Co Inc, Merck Res Labs, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 16期

关键词：

NATURAL-PRODUCT HENNOXAZOLE; RING-CHAIN TAUTOMERISM; HYDROXY-ALPHA-AMINO; PEPTIDE ANTIBIOTICS; AROMATIC-ALDEHYDES; MITSUNOBU REACTION; TRIFLUORIDE DAST; N-OXIDES; EFFICIENT; 2-OXAZOLINES;

D O I：

10.1021/ol101346w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An expedient method for the direct conversion of aldehydes to 2,4-disubstituted oxazoles is presented. The method relies on the oxidation of an oxazolidine formed from the condensation of serine with an aldehyde and proceeds through a 2,5-dihydrooxazole intermediate. In contrast to standard methods that start from carboxylic acids, the use of aldehydes as starting materials does not require intermediate purification and affords the oxazoles under relatively mild conditions.

引用

页码：3614 / 3617

页数：4

共 65 条

[1] SYNTHESIS OF SOME SUBSTITUTED 4-ACETYL-OXAZOLES AND CORRESPONDING ACIDS [J].

ALLAN, AW ;

WALTER, BH .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (12) :1397-&

[2]

Aoyama T, 1998, SYNLETT, P35

[3] SYNTHESIS OF OXAZOLIDINES, THIAZOLIDINES, AND 5,6,7,8-TETRAHYDRO-1H,3H-PYRROLO[1,2-C]OXAZOLE (OR THIAZOLE)-1,3-DIONES FROM BETA-HYDROXY-ALPHA-AMINO OR BETA-MERCAPTO-ALPHA-AMINO ACID-ESTERS [J].

BADR, MZA ;

ALY, MM ;

FAHMY, AM ;

MANSOUR, MEY .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (06) :1844-1847

[4] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[5] CUPRIC BROMIDE MEDIATED OXIDATION OF 4-CARBOXYOXAZOLINES TO THE CORRESPONDING OXAZOLES [J].

BARRISH, JC ;

SINGH, J ;

SPERGEL, SH ;

HAN, WC ;

KISSICK, TP ;

KRONENTHAL, DR ;

MUELLER, RH .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (16) :4494-4496

[6] UBER DIE DARSTELLUNG VON IMIDAZOL- UND OXAZOL-DERIVATEN DURCH OXIMKONDENSATIONEN [J].

BODENDORF, K ;

TOWLIATI, H .

ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1965, 298 (05) :293-+

[7] THE ACTION OF DIETHYLAMINOSULFUR TRIFLUORIDE (DAST) ON TRANS-4-AMIDO-3-CHROMANOLS - PREPARATION OF CIS-AMIDOALCOHOLS VIA OXAZOLINES [J].

BURRELL, G ;

EVANS, JM ;

JONES, GE ;

STEMP, G .

TETRAHEDRON LETTERS, 1990, 31 (25) :3649-3652

[8] Synthesis of 2,4,5-trisubstituted oxazoles [J].

Cai, XH ;

Yang, HJ ;

Zhang, GL .

SYNTHESIS-STUTTGART, 2005, (10) :1569-1571

[9] A new method for the formation of 2,4-disubstituted oxazoles: internal transfer of oxidation state through a molecular framework [J].

Cardwell, KS ;

Hermitage, SA ;

Sjolin, A .

TETRAHEDRON LETTERS, 2000, 41 (21) :4239-4242

[10] Some new aspects of the Boyer reaction [J].

Chakraborty, R ;

Franz, V ;

Bez, G ;

Vasadia, D ;

Popuri, C ;

Zhao, CG .

ORGANIC LETTERS, 2005, 7 (19) :4145-4148

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