A general large scale synthesis of 2-alkyl-7-methoxyindoles

被引：13

作者：

Chen, BC ^{[1
]}

Hynes, J ^{[1
]}

Pandit, CR ^{[1
]}

Zhao, RL ^{[1
]}

Skoumbourdis, AP ^{[1
]}

Wu, H ^{[1
]}

Sundeen, JE ^{[1
]}

Leftheris, K ^{[1
]}

机构：

[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Discovery Chem, Princeton, NJ 08543 USA

来源：

HETEROCYCLES | 2001年 / 55卷 / 05期

关键词：

2-nitrobenzaldehyde; nitroalkane; 2; beta-dinitrostyrene; condensation; reductive cyclization;

D O I：

10.3987/COM-01-9162

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general method has been developed for the large scale synthesis of 2-alkyl-7-methoxyindoles and analogs. This method involves an efficient preparation of the key intermediates, 1-(2-nitroaryl)-2-nitroalkanols and 1-(2-nitroaryl)-2-nitroalkenes, and affords 2-alkyl-7-methoxyindoles and analogs in 3 steps with good overall yields.

引用

页码：951 / 960

页数：10

共 40 条

[1] SYNTHESIS OF ALPHA-MONOSUBSTITUTED INDOLES [J].

AUGUSTINE, RL ;

GUSTAVSE.AJ ;

WANAT, SF ;

PATTISON, IC ;

HOUGHTON, KS ;

KOLETAR, G .

JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (17) :3004-3011

[2] BIOSYNTHESIS .26. SYNTHETIC STUDIES ON STRUCTURAL MODIFICATION OF LATE BIOSYNTHETIC PRECURSORS FOR COLCHICINE [J].

BATTERSBY, AR ;

MCDONALD, E ;

STACHULSKI, AV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (12) :3053-3063

[3] LACTONES .2. THE STRUCTURE OF MELLEIN [J].

BLAIR, J ;

NEWBOLD, GT .

JOURNAL OF THE CHEMICAL SOCIETY, 1955, :2871-2875

[4] CYCLOPROPANE CHEMISTRY RELATED TO THE ALKALOID-CC-1065 [J].

BRYSON, TA ;

ROTH, GA .

TETRAHEDRON LETTERS, 1988, 29 (18) :2167-2170

[5] THE SYNTHESIS OF DERIVATIVES OF 5-6-DIHYDROXYINDOLE .1. 5-6-METHYLENEDIOXYINDOLE AND ITS 2-METHYL DERIVATIVE [J].

BURTON, H ;

DUFFIELD, JA .

JOURNAL OF THE CHEMICAL SOCIETY, 1949, (JAN) :78-79

[6] Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents [J].

Caldarelli, M ;

Habermann, J ;

Ley, SV .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02) :107-110

[7] STUDIES ON THE SYNTHESIS OF THE ANTITUMOR AGENT CC-1065 - SYNTHESIS OF PDE-I AND PDE-II, INHIBITORS OF CYCLIC ADENOSINE-3',5'-MONOPHOSPHATE PHOSPHODIESTERASE USING THE 3,3'-BIPYRROLE STRATEGY [J].

CARTER, P ;

FITZJOHN, S ;

HALAZY, S ;

MAGNUS, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (09) :2711-2717

[8] Synthesis and cytotoxicity of analogues of the antibiotic BE 10988 inhibitors of DNA topoisomerase II [J].

Catrycke, MO ;

Houssin, R ;

Hénichart, JP ;

Pfeiffer, B ;

Renard, P ;

Dassonneville, L ;

Bailly, C .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (14) :2025-2030

[9] SOME OBSERVATIONS ON THE FORMATION OF 1-HYDROXYINDOLES IN THE LEIMGRUBER-BATCHO INDOLE SYNTHESIS [J].

CLARK, RD ;

REPKE, DB .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1985, 22 (01) :121-125

[10]

CLARK RD, 1991, SYNTHESIS-STUTTGART, P871

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