A new ring system: 3-H-pyrazolo[3,4-h]isoquinoline. An unexpected product from diazotization of an aminoisoquinoline

被引：1

作者：

Miller, RB

Stowell, JG

Jenks, CW

Farmer, SC

Wujcik, CE

Olmstead, MM

机构：

[1] Department of Chemistry, University of California, Davis

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 24期

关键词：

D O I：

10.1039/cc9960002711

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Diazotization of 7-amino-5,8-dimethyl-6-thiophenylisoquinoline with sodium nitrite in acetic acid gives a mixture of 6-thiaellipticine and 5-methyl-4-thiophenyl-3H-pyrazolo[3,4-h]isoquinoline, a new heterocyclic ring system whose crystal structure is presented.

引用

收藏

页码：2711 / 2712

页数：2

相关论文

共 19 条

[1] DIAZOTIZATION OF HETEROCYCLIC PRIMARY AMINES [J].

BUTLER, RN .

CHEMICAL REVIEWS, 1975, 75 (02) :241-257

[2] SYNTHESIS OF THIA-ELLIPTICINE 5,11-DIMETHYLBENZOTHIENO[2,3-G]ISOQUINOLINE [J].

FUJIWARA, AN ;

ACTON, EM ;

GOODMAN, L .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (06) :853-&

[3] SYNTHESIS OF ISOELLIPTICINE 5,11-DIMETHYL-10H-PYRIDO[3,4-B]CARBAZOLE [J].

FUJIWARA, AN ;

ACTON, EM ;

GOODMAN, L .

JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (01) :126-&

[4]

GODARD A, 1995, HETEROCYCLES, V40, P1055

[5]

Gribble G.W., 1990, The Alkaloids, V39, P239, DOI [DOI 10.1016/S0099-9598(08)60169-8, DOI 10.1021/jo200134a]

[6] SYNTHESES AND DIELS-ALDER CYCLOADDITION REACTIONS OF 4H-FURO[3,4-B]INDOLES - A REGIOSPECIFIC DIELS-ALDER SYNTHESIS OF ELLIPTICINE [J].

GRIBBLE, GW ;

KEAVY, DJ ;

DAVIS, DA ;

SAULNIER, MG ;

PELCMAN, B ;

BARDEN, TC ;

SIBI, MP ;

OLSON, ER ;

BELBRUNO, JJ .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5878-5891

[7] A VERSATILE AND EFFICIENT CONSTRUCTION OF THE 6H-PYRIDO[4,3-B]CARBAZOLE RING-SYSTEM - SYNTHESES OF THE ANTITUMOR ALKALOIDS ELLIPTICINE, 9-METHOXYELLIPTICINE, AND OLIVACINE AND THEIR ANALOGS [J].

GRIBBLE, GW ;

SAULNIER, MG ;

OBAZANUTAITIS, JA ;

KETCHA, DM .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5891-5899

[8]

HEGARTY AF, 1978, CHEM FUNCTIONAL GROU, P561

[9] A REGIOSPECIFIC TOTAL SYNTHESIS OF ELLIPTICINE VIA NITRENE INSERTION [J].

MILLER, RB ;

DUGAR, S .

TETRAHEDRON LETTERS, 1989, 30 (03) :297-300

[10] TOTAL SYNTHESIS OF ELLIPTICINE AND 9-METHOXYELLIPTICINE VIA BENZOTRIAZOLE INTERMEDIATES [J].

MILLER, RB ;

STOWELL, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (06) :886-888