Solid phase synthesis of benzimidazolones

被引：62

作者：

Wei, GP ^{[1
]}

Phillips, GB ^{[1
]}

机构：

[1] Berlex Biosci, Richmond, CA 94804 USA

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4039(97)10518-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient solid phase synthesis of benzimidazol-2-one-5 carboxylic acid is described. Polymer bound o-fluoronitroaromatic compound 2 was treated with an amine to give o-nitroaniline derivative 3. Reduction of 3 with SnCl2 followed by cyclization with DSC gave the benzimidazolone 5. Reaction with NaH and an alkyl bromide followed by cleavage with TFA gave 7. A library of 13 benzimidazolones has been prepared in three steps in 90-100 % crude yield and 91-95 % purity. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：179 / 182

页数：4

共 14 条

[1] DANKWARDT SM, 1995, TETRAHEDRON LETT, V36, P4923, DOI 10.1016/0040-4039(95)00930-B
[2] SOLID-PHASE PEPTIDE-SYNTHESIS UTILIZING 9-FLUORENYLMETHOXYCARBONYL AMINO-ACIDS
FIELDS, GB
NOBLE, RL
[J]. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1990, 35 (03): : 161 - 214
[3] Organic chemistry on solid supports
Fruchtel, JS
Jung, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01): : 17 - 42
[4] Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery
Gordon, EM
Gallop, MA
Patel, DV
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) : 144 - 154
[5] REDUCTION OF AROMATIC NITRO-COMPOUNDS TO AMINES WITH SODIUM BOROHYDRIDE COPPER(II) ACETYLACETONATE
HANAYA, K
MURAMATSU, T
KUDO, H
CHOW, YL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (10): : 2409 - 2410
[6] Solid phase synthesis of 3,4-disubstituted-7-carbamoyl-1,2,3,4-tetrahydroquinoxalin-2-ones
Lee, J
Murray, WV
Rivero, RA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) : 3874 - 3879
[7] Madden Dave, 1995, Perspectives in Drug Discovery and Design, V2, P269, DOI 10.1007/BF02172067
[8] The current status of heterocyclic combinatorial libraries
Nefzi, A
Ostresh, JM
Houghten, RA
[J]. CHEMICAL REVIEWS, 1997, 97 (02) : 449 - 472
[9] Solid phase synthesis of benzimidazoles
Phillips, GB
Wei, GP
[J]. TETRAHEDRON LETTERS, 1996, 37 (28) : 4887 - 4890
[10] PRESTON PN, 1981, HETEREOCYCLIC COMPOU, V40

← 1 2 →