An efficient solid-phase of 3-alkylamino-1,2,4-oxadiazoles

被引：11

作者：

Makara, GM ^{[1
]}

Schell, P ^{[1
]}

Hanson, K ^{[1
]}

Moccia, D ^{[1
]}

机构：

[1] NeoGenesis Pharmaceut Inc, Cambridge, MA 02139 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 29期

关键词：

benzotriazole; combinatorial; solid-phase; oxadiazole;

D O I：

10.1016/S0040-4039(02)01016-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A solid-phase synthesis of substituted 3-alkylamino-1,2,4-oxadiazoles has been developed. The synthesis utilizes immobilized N-acyl-1H-benzotriazole-1-arboximidamides as key intermediates. Cyclization with hydroxylamine under mild conditions furnished the oxadiazole skeleton regioselectively in high yield and purity. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：5043 / 5045

页数：3

相关论文

共 18 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].

AbdelMagid, AF ;

Carson, KG ;

Harris, BD ;

Maryanoff, CA ;

Shah, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862

[2]

Atsushi K, 1993, Patent publication, VWO9313083A1, Patent No. 9313083

[3] PHOTOCHEMICAL BEHAVIOR OF SOME 1,2,4-OXADIAZOLE DERIVATIVES [J].

BUSCEMI, S ;

CICERO, MG ;

VIVONA, N ;

CARONNA, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (06) :1313-1315

[4] Fluoro heterocycles.: A photochemical methodology for the synthesis of 3-amino- and 3-(N-alkylamino)-5-perfluoroalkyl-1,2,4-oxadiazoles [J].

Buscemi, S ;

Pace, A ;

Vivona, N .

TETRAHEDRON LETTERS, 2000, 41 (41) :7977-7981

[5] PHOTOINDUCED MOLECULAR-REARRANGEMENTS - SOME INVESTIGATIONS OF THE PHOTOCHEMICAL BEHAVIOR OF 3-(ACYLAMINO)-1,2,5-OXADIAZOLES (FURAZANS) [J].

BUSCEMI, S ;

VIVONA, N ;

CARONNA, T .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (13) :4096-4101

[6] Novel 1,2,4-oxadiazoles as potent and selective histamine H-3 receptor antagonists [J].

Clitherow, JW ;

Beswick, P ;

Irving, WJ ;

Scopes, DIC ;

Barnes, JC ;

Clapham, J ;

Brown, JD ;

Evans, DJ ;

Hayes, AG .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (07) :833-838

[7] Parallel synthesis of 1,2,4-oxadiazoles using CDI activation [J].

Deegan, TL ;

Nitz, TJ ;

Cebzanov, D ;

Pufko, DE ;

Porco, JA .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (02) :209-212

[8] OXADIAZOLES AS ESTER BIOISOSTERIC REPLACEMENTS IN COMPOUNDS RELATED TO DISOXARIL - ANTIRHINOVIRUS ACTIVITY [J].

DIANA, GD ;

VOLKOTS, DL ;

NITZ, TJ ;

BAILEY, TR ;

LONG, MA ;

VESCIO, N ;

ALDOUS, S ;

PEVEAR, DC ;

DUTKO, FJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (15) :2421-2436

[9] Synthesis of oxadiazoles on solid support [J].

Hébert, N ;

Hannah, AL ;

Sutton, SC .

TETRAHEDRON LETTERS, 1999, 40 (49) :8547-8550

[10] KINETICS AND MECHANISM OF HYDROLYSIS OF AMIDINATING AGENT, 1-(N1-BENZOYLAMIDINO)-3,5-DIMETHYLPYRAZOLE [J].

HEGARTY, AF ;

HEGARTY, CN .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (15) :2054-2060