CINNOLINES .X. OXIDATIVE-REARRANGEMENT OF 1-AMINOOXINDOLES TO 3-CINNOLINOLS

被引：15

作者：

BAUMGARTEN, HE

WITTMAN, WF

LEHMANN, GJ

机构：

[1] Department of Chemistry, University of Nebraska, Lincoln, Nebraska

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1969年 / 6卷 / 03期

关键词：

D O I：

10.1002/jhet.5570060311

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An improved route for the oxidative‐rearrangement of 1 ‐aminooxindoles, treatment with equimolar amounts of t‐butyl hypochlorite, produces nearly quantitative yields of 3‐cinnolinols of excellent purity. The syntheses of the previously inaccessible 4‐ and 6‐ehloro‐1‐armnooxin‐doles has shown that this method, first applied to 1‐aminooxindole, may be reasonably general. The mechanism of this reaction is discussed in terms of nitrene and nitrenoid intermediates. Copyright © 1969 Journal of Heterocyclic Chemistry

引用

收藏

页码：333 / +

页数：1

相关论文

共 19 条

[1] CINNOLINES .31. THE NATURE OF THE C(3)-POSITION - SOME EXPERIMENTS WITH 3-SUBSTITUTED CINNOLINES [J].

ALFORD, EJ ;

SCHOFIELD, K .

JOURNAL OF THE CHEMICAL SOCIETY, 1953, (JUN) :1811-1817

[2] ADDITION OF NITRENES TO ACETYLENES . ANTI-AROMATICITY OF 1H-AZIRINES [J].

ANDERSON, DJ ;

GILCHRIS.TL ;

REES, CW .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (04) :147-&

[3]

ANDERSON DJ, 1969, CHEM COMMUN, P149

[4] STEREOSPECIFIC ADDITION OF AN AMINO-NITRENE TO MONO- AND DI-ENES [J].

ATKINSON, RS ;

REES, CW .

CHEMICAL COMMUNICATIONS, 1967, (23) :1230-&

[5] REACTIONS OF LEAD TETRA-ACETATE .16. OXIDATION OF MONOACYLHYDRAZINES [J].

AYLWARD, JB ;

NORMAN, ROC .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (18) :2399-&

[6] CINNOLINES .8. REACTION OF 3-AMINOCINNOLINES AND 3-AMINOISOQUINOLINE WITH NITROUS ACID [J].

BAUMGARTEL, H ;

DIRKS, JE ;

MURDOCK, WF .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (03) :803-&

[7] CINNOLINES .2. 4-HYDROXY-3-NITROCINNOLINE AND DERIVATIVES [J].

BAUMGARTEN, HE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (19) :5109-5112

[8] CINNOLINES .6. THE STRUCTURE OF NEBER LACTAM - A NEW SYNTHESIS OF 3-CINNOLINOL [J].

BAUMGARTEN, HE ;

CREGER, PL ;

ZEY, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (15) :3977-3982

[9] OXIDATION OF 1- AND 2-AMINOBENZOTRIAZOLE [J].

CAMPBELL, CD ;

REES, CW .

CHEMICAL COMMUNICATIONS, 1965, (10) :192-&

[10]

CAMPBELL CD, 1964, P CHEM SOC LONDON, P296