A convenient preparation of functionalized 1,8-dioxygenated naphthalenes from 6-alkoxybenzocyclobutenones

被引：15

作者：

Bungard, CJ ^{[1
]}

Morris, JC ^{[1
]}

机构：

[1] Univ Canterbury, Dept Chem, Christchurch 1, New Zealand

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 07期

关键词：

D O I：

10.1021/jo015887b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An alternate route for the synthesis of naphthalene building blocks 1-4 has been developed, starting from readily available 6-alkoxybenzocyclobutenones. As thermolysis of a propynylbenzocyclobutenol only provided the naphthalene in low yield, allenyl-substituted benzocyclobutenols were investigated. The desired allenic precursors were prepared by a two-step procedure, which involved hydroxyl-directed reduction of the chloropropargylbenzocyclobutenols obtained from addition of lithiopropargyl chloride to the benzocyclobutenones. Thermolysis of the allenic alcohols gave the desired naphthalenes in good yields.

引用

页码：2361 / 2364

页数：4

共 21 条

[1] Acetogenic isoquinoline alkaloids, part 147.: First total synthesis of the 7,6′-coupled antifungal naphthylisoquinoline alkaloid dioncophylline B
Bringmann, G
Günther, C
Peters, EM
Peters, K
[J]. TETRAHEDRON, 2001, 57 (07) : 1253 - 1259
[2] Bringmann G, 1999, SYNLETT, P216
[3] Bringmann G, 2000, SYNTHESIS-STUTTGART, P383
[4] ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B
BRINGMANN, G
GOTZ, R
KELLER, PA
WALTER, R
HENSCHEL, P
SCHAFFER, M
STABLEIN, M
KELLY, TR
BOYD, MR
[J]. HETEROCYCLES, 1994, 39 (02) : 503 - 508
[5] BRINGMANN G, 1995, ALKALOIDS, V46, pCH4
[6] Bungard CJ, 2001, SYNTHESIS-STUTTGART, P741
[7] CONVENIENT GENERATION OF 1-PROPYNYLLITHIUM - ONE-POT SYNTHESIS OF ACETYLENIC CARBINOLS FROM 1,2-DIBROMOPROPANE AND ALDEHYDES AND KETONES
GRIBBLE, GW
JOYNER, HH
SWITZER, FL
[J]. SYNTHETIC COMMUNICATIONS, 1992, 22 (20) : 2997 - 3002
[8] Accelerating effect of meta substituents in the ester-mediated nucleophilic aromatic substitution reaction
Hattori, T
Takeda, A
Suzuki, K
Koike, N
Koshiishi, E
Miyano, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (22): : 3661 - 3671
[9] The preparation of substituted 3,4-dihydro-1(2H)-naphthalenones from benzocyclobutenones via sequential thermal electrocyclic reactions
Hickman, DN
Hodgetts, KJ
Mackman, PS
Wallace, TW
Wardleworth, JM
[J]. TETRAHEDRON, 1996, 52 (06) : 2235 - 2260
[10] HORII Z, 1963, J CHEM SOC, P3941

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