A two-stage iterative process for the synthesis of poly-oxazoles

被引：53

作者：

Atkins, JM ^{[1
]}

Vedejs, E ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 15期

关键词：

D O I：

10.1021/ol051244x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Methodology has been developed to prepare bis-oxazoles via a two-stage iterative process. The sequence begins with C-2-chlorination of a lithiated oxazole using hexachloroethane. Generation of the C-2-C-4, bond by SNAr substitution with TosMIC anion, followed by conversion to the heterocycle in a one-pot reaction with glyoxylic acid monohydrate, affords the desired bis-oxazole in good yield and purity. The two-stage process allows for efficient synthesis of a tris-oxazole and the first iterative preparation of a tetra-oxazole.

引用

页码：3351 / 3354

页数：4

共 49 条

[1] Application of palladium(0)-catalyzed processes to the synthesis of oxazole-containing partial ergot alkaloids
Anderson, BA
Becke, LM
Booher, RN
Flaugh, ME
Harn, NK
Kress, TJ
Varie, DL
Wepsiec, JP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) : 8634 - 8639
[2] Anderson BA, 1996, SYNTHESIS-STUTTGART, P583
[3] Studies towards the synthesis of diazonamide A. Synthesis of the indole bis-oxazole fragment
Bagley, MC
Hind, SL
Moody, CJ
[J]. TETRAHEDRON LETTERS, 2000, 41 (35) : 6897 - 6900
[4] BARRETT AGM, 1995, SYNLETT, P415
[5] A new synthesis of chloroheterocycles via metal-halogen exchange between trichloroacetyl derivatives and heteroaromatic lithium and Grignard reagents
Boga, C
Del Vecchio, E
Forlani, L
Milanesi, L
Todesco, PE
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 588 (02) : 155 - 159
[6] Tetrahalogenomethanes: simple reagents for the synthesis of monohalogenated and mixed dihalogenated aromatic heterocycles via metal-halogen exchange from lithium compounds
Boga, C
Del Vecchio, E
Forlani, L
Todesco, PE
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 601 (02) : 233 - 236
[7] A concise and flexible total synthesis of (-)-diazonamide A
Burgett, AWG
Li, QY
Wei, Q
Harran, PG
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (40) : 4961 - 4966
[8] Asymmetric synthesis of a C1-C19 fragment of ulapualide A
Celatka, CA
Panek, JS
[J]. TETRAHEDRON LETTERS, 2002, 43 (39) : 7043 - 7046
[9] Chattopadhyay SK, 1997, SYNLETT, P1342
[10] Metalated heterocycles and their applications in synthetic organic chemistry
Chinchilla, R
Nájera, C
Yus, M
[J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2667 - 2722

← 1 2 3 4 5 →