Cyclization of o-(3-hydroxy-3-methylbutynyl)phenols with boron tribromide to 4-bromo-2,2-dimethylchromenes and their electroreduction to 2,2-dimethylchromenes

被引：11

作者：

Tsukayama, M ^{[1
]}

Utsumi, H ^{[1
]}

Kunugi, A ^{[1
]}

Nozaki, H ^{[1
]}

机构：

[1] OKAYAMA UNIV SCI,FAC SCI,OKAYAMA 700,JAPAN

来源：

HETEROCYCLES | 1997年 / 45卷 / 06期

关键词：

D O I：

10.3987/COM-97-7804

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cyclization of o-(3-hydroxy-3-methylbutynyl)phenols (2) with boron tribromide gave easily 4-bromo-2,2-dimethylchromenes (3). Electrolytic reduction of 3 at a Hg-pool electrode afforded the corresponding 2,2-dimethylchromenes (6) in high yields.

引用

页码：1131 / 1142

页数：12

共 38 条

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[33] Synthesis and Crystal Structure of Spiro[1-bromo(S)-4-(R)-hydroxy-5-oxa-6-oxo-bicyclo[3.1.0]hexane-2,2'-(3'-diethyl-α-(S)-4''-Cl-benzyloxyphosphonyl-4'-(1R,2S,5R)-menthyloxybutyrolactone)]
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[34] Synthesis and Crystal Structure of Spiro[1-bromo(S)-4-(R)-hydroxy-5-oxa-6-oxo-bicyclo[3.1.0]hexane-2,2'-(3'-diethyl-α-(S)-4''-Cl-benzyloxyphosphonyl-4'-(1R,2S,5R)-menthyloxybutyrolactone)]
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[35] Crystal structure of (-)-N-[(3R,4S)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl]-N-methyl-ethansulfonamide hydrate, (CN)C9OH5(CH3)2(OH)N(CH3)SO2C2H5 • 0.34H2O
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[36] (Anilino{(Z)-2-[(E)-5-bromo-3-methoxy-2-oxidobenzylidene]hydrazin-1-ylidene-kappa O-2(2),N-2}methanethiolato-kappa S)(4,4'-di-methyl-2,2'-bipyridine-kappa N-2,N')zinc N,N-dimethylformamide monosolvate
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[37] Synthesis and crystal structure of Cu3(Bipy)2(L1)2(L2)2⋅ 4H2O(Bipy = 2,2′-bipyridine, L1 =1-((2-sulfonateethylimino)methyl)-2-naphthol), L2 = 2-hydroxy-1-naphthaldehyde)
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[38] Synthesis and crystal structure of Cu3(Bipy)2(L1)2(L2)2•4H2O(Bipy=2,2′-bipyridine, L1=1-((2-sulfonate-ethylimino)methyl)-2-naphthol), L2=2-hydroxy-1-naphthaldehyde)
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