SYNTHESIS OF 4-AMINOPYRIMIDINES FROM 1,2,4-OXADIAZOLES .5. REDUCTIVE FORMATION OF 2-(BENZOYLAMINO)INDOLE FROM 3-(2-AMINOBENZYL)-5-PHENYL-1,2,4-OXADIAZOLE AND ITS TRANSFORMATION TO 6-PHENYL-8H-PYRIMIDO-[1,6-A-4,5-B']DIINDOLE, A NEW HETEROCYCLIC RING-SYSTEM

被引：8

作者：

BATA, I

KORBONITS, D

KOLONITS, P

PODANYI, B

TAKACSYEROS, T

SIMON, K

机构：

[1] CHINOIN CHEM & PHARMACEUT WORKS LTD,POB 110,H-1325 BUDAPEST,HUNGARY

[2] TECH UNIV BUDAPEST,INST ORGAN CHEM,H-1521 BUDAPEST,HUNGARY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 08期

关键词：

1,2,4-OXADIAZOLES, 5-SUBSTITUTED, 3-(2-AMINOBENZYL)-5-PHENYL-1,2,4-OXADIAZOLE; INDOLES; 2-(ACYLAMINO)INDOLES; 8H-PYRIMIDO[1,6-A-4,5-B']DIINDOLES, 6-ARYL;

D O I：

10.1002/cber.19931260814

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Catalytic hydrogenation of 5-substituted 3-(2-aminobenzyl)-1,2,4-oxadiazoles 7 give 2-(acylamino)indoles 10. Treatment of 2-(benzoylamino)indoles 10a-c with acid leads to the novel 6-phenyl-8H-pyrimido[1,6-a: 4,5-b]diindoles 19a-c, A route for the new ring formation is proposed. Catalytic hydrogenation of 19a (Raney nickel, 70-degrees-C, atmospheric pressure) saturates the 6-phenyl ring but leaves the pentacyclic rig system intact. The structure of 19a is confirmed by an X-ray crystallographic analysis.

引用

页码：1835 / 1841

页数：7

共 41 条

[1] HETEROCYCLIC REARRANGEMENTS .14. ATTEMPTS TO ACTIVATE RING-OPENING-RING-CLOSURE REARRANGEMENTS WITH CARBON AS CENTRAL ATOM [J].

AFRIDI, AS ;

KATRITZKY, AR ;

RAMSDEN, CA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (03) :315-320

[2]

ASINGER F, 1970, METHODEN ORG CHEM HO, V5, P62

[3] FORMATION OF ALPHA-(ACYLAMINO)BUTYRAMIDE OXIMES FROM 5-SUBSTITUTED 3-(1-AMINOPROPYL)-1,2,4-OXADIAZOLES - AN ASTONISHING HYDROLYTIC TRANSFORMATION [J].

BAKO, EM ;

HORVATH, K ;

PALOSI, E ;

KORBONITS, D .

CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (04) :723-726

[4] RING TRANSFORMATION OF 1-[(1,2,4-OXADIAZOL-3-YL)METHYL]ISOQUINOLINES INTO 2-ACYLAMINOPYRAZOLO[5,1-A]ISOQUINOLINES [J].

BATA, I ;

HEJA, G ;

KISS, P ;

KORBONITS, D .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (01) :9-12

[5] HETEROCYCLIC REARRANGEMENTS .X. A GENERALISED MONOCYCLIC REARRANGEMENT [J].

BOULTON, AJ ;

KATRITZK.AR ;

HAMID, AM .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1967, (20) :2005-&

[6]

BOULTON AJ, 1974, LECTURES HETEROCYCLI, V2, P45

[7]

FREIFELDER M, 1971, PRACTICAL CATALYTIC, P544

[8]

Glushkov R. G., 1967, KHIM FARM ZH, V1, P25

[9]

HODGSON HH, 1948, J CHEM SOC, P242

[10]

HORVATH K, 1986, J MOL STRUC-THEOCHEM, V136, P215

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