Preparation of alkyl 4,5-dihydro-2H-benz[g]indazole-2-carboxylates and methyl 4,5-dihydro-2H-benz[e]indazole-2-carboxylates from dilithiated 1-tetralone or 2-tetralone carboalkoxyhydrazones and aromatic esters

被引：8

作者：

Grant, SP ^{[1
]}

Embree, MC ^{[1
]}

Downs, JR ^{[1
]}

Townsend, JD ^{[1
]}

Beam, CF ^{[1
]}

机构：

[1] Coll Charleston, Dept Chem & Biochem, Charleston, SC 29424 USA

来源：

INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH | 2003年 / 42卷 / 23期

关键词：

D O I：

10.1021/ie010629q

中图分类号：

TQ [化学工业];

学科分类号：

0817 ;

摘要：

Dilithiated 1-tetralone or 2-tetralone carboalkoxyhydrazones were prepared in excess lithium diisopropylamide and condensed with a variety of aromatic esters followed by acid cyclization of C-acylated intermediates to give substituted dihydrobenzindazoles, alkyl 4,5-dihydro-2H-benz-[g]indazole-2-carboxylates and methyl 4,5-dihydro-2H-benz[e]indazole-2-carboxylates. These fused-ring heterocyclic products have considerable application potential.

引用

页码：5721 / 5726

页数：6

共 93 条

[1] PERICYCLIC SYNTHESIS AND EXPLORATORY PHOTOCHEMISTRY OF POTENTIALLY DIRECT PROGENITORS OF UNRESTRICTED HETERO[11]ANNULENE SYSTEM [J].

ANASTASSIOU, AG ;

REICHMANIS, E ;

GIRGENTI, SJ ;

SCHAEFERRIDDER, M .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) :315-322

[2] The preparation of 4,5-dihydro-2H-benz[e]indazoles from dilithiated 2-tetralone phenylhydrazone and aromatic esters [J].

Angel, AJ ;

Finefrock, AE ;

Williams, AR ;

Townsend, JD ;

Nguyen, THV ;

Hurst, DR ;

Heldrich, FJ ;

Beam, CF ;

Badejo, IT .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (05) :1231-1233

[3] ATZ1993, an orally active and novel nonpeptide antagonist for endothelin receptors and inhibition of intimal hyperplasia after balloon denudation of the rabbit carotid artery [J].

Azuma, H ;

Sato, J ;

Masuda, H ;

Goto, M ;

Tamaoki, S ;

Sugimoto, A ;

Hamasaki, H ;

Yamashita, H .

JAPANESE JOURNAL OF PHARMACOLOGY, 1999, 81 (01) :21-28

[4] 1H-CYCLOBUTA[DE]NAPHTHALENE (1,8-METHANONAPHTHALENE) [J].

BAILEY, RJ ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8116-8117

[5] CHEMISTRY OF 8-SUBSTITUTED 1-NAPHTHYLMETHYLENES AND 2-SUBSTITUTED BENZYLIDENES - A SIMPLE ENTRY TO 1H-CYCLOBUTA[DE]NAPHTHALENES [J].

BAILEY, RJ ;

CARD, PJ ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (19) :6096-6103

[6] CYCLIZATION AT LESS NUCLEOPHILIC CENTER OF A BETA-DIKETONE DICARBANION THROUGH A DICARBANION-BENZYNE INTERMEDIATE [J].

BEAM, CF ;

BISSELL, RL ;

HAUSER, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :2083-&

[7] THE PREPARATION AND REACTIONS OF C(ALPHA),N-DILITHIOCARBOALKOXYHYDRAZONES [J].

BEAM, CF ;

HALL, HL ;

HUFF, AM ;

TUMMONS, RC ;

OGRADY, SA .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (06) :1897-1899

[8] PREPARATION OF PYRAZOLES FROM C(ALPHA)NN-TRIANION OF HYDRAZONES HAVING AN ALPHA-HYDROGEN ATOM [J].

BEAM, CF ;

FOOTE, RS ;

HAUSER, CR .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (09) :1658-&

[9]

BEBBINGTON D, 2002, Patent No. 0222606

[10] NMR-STUDIES IN THE HETEROCYCLIC SERIES .31. EFFECT OF N-SUBSTITUENTS ON THE C-13 NMR PARAMETERS OF AZOLES [J].

BEGTRUP, M ;

ELGUERO, J ;

FAURE, R ;

CAMPS, P ;

ESTOPA, C ;

ILAVSKY, D ;

FRUCHIER, A ;

MARZIN, C ;

DEMENDOZA, J .

MAGNETIC RESONANCE IN CHEMISTRY, 1988, 26 (02) :134-151

← 1 2 3 4 5 6 7 8 9 10 →