Formation of 3,3,5,7-tetranitrooxindole and 3,5,7-trinitroindazole by nitration of oxindole

被引：14

作者：

Bergman, J ^{[1
]}

Bergman, S ^{[1
]}

机构：

[1] NOVUM, CNT, DEPT ORGAN CHEM, S-14157 HUDDINGE, SWEDEN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 51期

关键词：

D O I：

10.1016/S0040-4039(96)02139-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nitration (HNO3/H2SO4) of oxindole gave 3,3,5,7-tetranitrooxindole (1c), which readily underwent ring-opening and decarboxylation to 4,6-dinitro-2-(dinitromethyl)aniline (4b), which in turn could be cyclized to 3,5,7-trinitroindazole (5). Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：9263 / 9266

页数：4

相关论文

共 15 条

[1] QUINAMINE .4. SULPHOBENZENEAZOQUINAMINE AND NITRATION AND OXIDATION OF QUINAMINE TO 3-6-8-TRINITRO-4-HYDROXYQUINOLINE [J].

BENDZ, G ;

CULVENOR, CCJ ;

GOLDSWORTHY, LJ ;

KIRBY, KS ;

ROBINSON, R .

JOURNAL OF THE CHEMICAL SOCIETY, 1950, (APR) :1130-1138

[2] SYNTHESIS OF INDOLES VIA RING-CLOSURE OF 2-ALKYLNITROANILINE DERIVATIVES [J].

BERGMAN, J ;

SAND, P .

TETRAHEDRON, 1990, 46 (17) :6085-6112

[3] PREPARATION AND PROPERTIES OF 5-NITROOXINDOLE, 7-NITROOXINDOLE, AND 5,7-DINITROOXINDOLE [J].

COUTTS, RT ;

HINDMARS.KW ;

MAH, E .

CANADIAN JOURNAL OF CHEMISTRY, 1970, 48 (23) :3747-&

[4] SUR QUELQUES DERIVES DE LOXINDOLE ET DE LISATINE .1. SUR LES DERIVES NITRES EN POSITION-5 ET POSITION-6 [J].

GIOVANNINI, E ;

PORTMANN, P .

HELVETICA CHIMICA ACTA, 1948, 31 (05) :1375-1380

[5] DINITROMETHANE [J].

GRAKAUSKAS, V ;

GUEST, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (18) :3485-3488

[6]

Honey PJ, 1996, ACS SYM SER, V623, P134

[7]

KOLESETS.GI, 1970, ZH ORG KHIM+, V6, P334

[8]

LAIKHTER AL, 1991, ZH ORG KHIM, V27, P1849

[9]

Menon KN, 1930, J CHEM SOC, P830, DOI 10.1039/jr9300000830

[10] NITRATION OF INDOLES .3. POLYNITRATION OF 2-ALKYLINDOLES [J].

NOLAND, WE ;

SMITH, LR ;

RUSH, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (10) :3457-+