Synthesis of a pyrrolo[1,4]benzodiazepinequinone

被引：8

作者：

Tapia, RA ^{[1
]}

Centella, CR ^{[1
]}

Valderrama, JA ^{[1
]}

机构：

[1] Pontificia Univ Catolica Chile, Fac Quim, Santiago 22, Chile

来源：

SYNTHETIC COMMUNICATIONS | 1999年 / 29卷 / 12期

关键词：

D O I：

10.1080/00397919908086212

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Condensation of 3,6-dimethoxy-2-nitrobenzoyl chloride with L-proline methyl ester afforded amide 4, which underwent reductive cyclization with iron(II) sulfate and ammonium hydroxide to yield pyrrolobenzodiazepine 5. Oxidation of 5 with ammonium cerium(IV) nitrate led to the new heterocyclic quinone 6 in 53% overall yield.

引用

页码：2163 / 2168

页数：6

共 17 条

[1] 3,6-DIMETHOXYBENZOCYCLOBUTENONE - A VERSATILE QUINONE PRECURSOR [J].

AZADIARDAKANI, M ;

WALLACE, TW .

TETRAHEDRON LETTERS, 1983, 24 (17) :1829-1832

[2]

BERDY J, 1980, CRC HDB ANTIBIOTIC C, V3, P315

[3] SOME DERIVATIVES OF 2,5-DIMETHOXYACETOPHENONE [J].

BOST, RW ;

HOWE, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (12) :5864-5865

[4] HETEROCYCLIC QUINONES .17. A NEW INVIVO ACTIVE ANTINEOPLASTIC DRUG - 6,7-BIS(1-AZIRIDINYL)-4-[[3-(N,N-DIMETHYLAMINO)PROPYL]AMINO]-5,8-QUINAZOLINEDIONE [J].

GIORGIRENAULT, S ;

RENAULT, J ;

GEBELSERVOLLES, P ;

BARON, M ;

PAOLETTI, C ;

CROS, S ;

BISSERY, MC ;

LAVELLE, F ;

ATASSI, G .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (01) :38-46

[5]

HOWE CA, 1965, J CHEM SOC, P795

[6] PYRROLO(1,4)BENZODIAZEPINE ANTITUMOR ANTIBIOTICS - COMPARATIVE ASPECTS OF ANTHRAMYCIN, TOMAYMYCIN AND SIBIROMYCIN [J].

HURLEY, LH .

JOURNAL OF ANTIBIOTICS, 1977, 30 (05) :349-370

[7]

Kitahara Y, 1997, CHEM PHARM BULL, V45, P1697

[8] Streptonigrin and related compounds .6. Synthesis and activity of some quinoxaline analogues [J].

Rao, KV ;

Rock, CP .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1996, 33 (02) :447-458

[9]

REMERS WA, 1979, CHEM ANTITUMOR ANTIB, V1, P221

[10]

TAO XL, 1994, TETRAHEDRON, V50, P2017

← 1 2 →