4-HYDROXY-2-METHYL-3(2H)-ISOTHIAZOLONE-1,1-DIOXIDE AS PROTECTING GROUP OF 4-(N-METHYLAMINOSULFONYL)METHYLPHENYLHYDRAZINE DURING FISCHER INDOLE SYNTHESIS

被引：18

作者：

REMUZON, P

DUSSY, C

JACQUET, JP

SOUMEILLANT, M

BOUZARD, D

机构：

[1] Bristol-Myers Squibb, Pharmaceutical Research Institute, Chemical Process Research, 77422 Marne-La-Vallée Cedex 2

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 35期

关键词：

D O I：

10.1016/0040-4039(95)01269-N

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Protection of the benzylic position of 4-methylaminosulfonylmethylphenyl hydrazine 6 with a 4-hydroxy-2-methyl-3(2H)-isothiazolone-1,1-dioxide group allowed the preparation of indole 3 without formation of side-product.

引用

页码：6227 / 6230

页数：4

共 10 条

[1]

[Anonymous], 1970, CHEM INDOLES

[2] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 3-[2-(DIMETHYLAMINO)ETHYL]-5-[(1,1-DIOXO-5-METHYL-1,2,5-THIADIAZOLIDIN-2-YL)-METHYL]-1H-INDOLE AND ANALOGS - AGONISTS FOR THE 5-HT1D RECEPTOR [J].

CASTRO, JL ;

BAKER, R ;

GUIBLIN, AR ;

HOBBS, SC ;

JENKINS, MR ;

RUSSELL, MGN ;

BEER, MS ;

STANTON, JA ;

SCHOLEY, K ;

HARGREAVES, RJ ;

GRAHAM, MI ;

MATASSA, VG .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (19) :3023-3032

[3] SYNTHESIS, BIOLOGICAL-ACTIVITY AND ELECTROSTATIC PROPERTIES OF 3-[2-(DIMETHYLAMINO)ETHYL]-5-[(3-AMINO-1,2,4-THIADIAZOL-5-YL)METHYL]-1H-INDOLE, A NOVEL 5-HT1D RECEPTOR AGONIST [J].

CASTRO, JL ;

MATASSA, VG ;

BROUGHTON, HB ;

MOSLEY, RT ;

STREET, LJ ;

BAKER, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (06) :993-997

[4] METHIODIDE APPROACH TO THE SYNTHESIS OF 3-[2-(DIMETHYLAMINO)ETHYL]-5-[(1,1-DIOXO-5-METHYL-1,2,5-THIADIAZOLIDIN-2-YL)METHYL]-1H-INDOLE AND ANALOGS [J].

CASTRO, JL ;

MATASSA, VG .

TETRAHEDRON LETTERS, 1993, 34 (29) :4705-4708

[5] IMPROVED FISCHER INDOLE REACTION FOR THE PREPARATION OF N,N-DIMETHYLTRYPTAMINES - SYNTHESIS OF L-695,894, A POTENT 5-HT1D RECEPTOR AGONIST [J].

CHEN, CY ;

SENANAYAKE, CH ;

BILL, TJ ;

LARSEN, RD ;

VERHOEVEN, TR ;

REIDER, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) :3738-3741

[6]

DELIGANIS AV, 1991, HEADACHE, V31, P228

[7] THE DEVELOPMENT OF A HIGHLY SELECTIVE 5-HT(1) RECEPTOR AGONIST, SUMATRIPTAN, FOR THE TREATMENT OF MIGRAINE [J].

FENIUK, W ;

HUMPHREY, PPA .

DRUG DEVELOPMENT RESEARCH, 1992, 26 (03) :235-240

[8] THE SYNTHESIS OF A CONFORMATIONALLY RESTRICTED ANALOG OF THE ANTIMIGRAINE DRUG SUMATRIPTAN [J].

MACOR, JE ;

BLANK, DH ;

POST, RJ ;

RYAN, K .

TETRAHEDRON LETTERS, 1992, 33 (52) :8011-8014

[9] 5-ARYL-4-HYDROXY-3(2H)-ISOTHIAZOLONE 1,1-DIOXIDE DERIVATIVES - SYNTHESIS AND C-13 NMR CHARACTERIZATION [J].

ROONEY, CS ;

COCHRAN, DW ;

ZIEGLER, C ;

CRAGOE, EJ ;

WILLIAMS, HWR .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (12) :2212-2217

[10]

WILLY WE, 1983, B SOC CHIM FR, P41

← 1 →