Silver(I)-catalyzed novel cascade cyclization reactions: Incorporation of allenes into the isochromenes

被引：64

作者：

Patil, NT ^{[1
]}

Pahadi, NK ^{[1
]}

Yamamoto, Y ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Sci, Dept Chem, Sendai, Miyagi 9808578, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 24期

关键词：

D O I：

10.1021/jo051524q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The silver(I)-catalyzed reaction of alkynones with alcohols represents a general tool for the synthesis of 1-allenyl isochromenes. The reaction most probably proceeds via the formation of benzopyrylium cation, which subsequently undergoes nucleophilic attack of an alcohol to give the annulation products.

引用

页码：10096 / 10098

页数：3

共 55 条

[1] Palladium-catalyzed hydrocarboxylation of allenes [J].

Al-Masum, M ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (15) :3809-3810

[2] The two component palladium catalyst system for intermolecular hydroamination of allenes [J].

AlMasum, M ;

Meguro, M ;

Yamamoto, Y .

TETRAHEDRON LETTERS, 1997, 38 (34) :6071-6074

[3] AuBr3-catalyzed [4+2] benzannulation between an enynal unit and enol [J].

Asao, N ;

Aikawa, H ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (24) :7458-7459

[4] Pd(II) acts simultaneously as a Lewis acid and as a transition-metal catalyst: Synthesis of cyclic alkenyl ethers from acetylenic aldehydes [J].

Asao, N ;

Nogami, T ;

Takahashi, K ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (05) :764-765

[5] Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].

Asao, N ;

Nogami, T ;

Lee, S ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925

[6] AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].

Asao, N ;

Takahashi, K ;

Lee, S ;

Kasahara, T ;

Yamamoto, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651

[7] Cyclization of carbonyl groups onto alkynes upon reaction with IPy2BF4 and their trapping with nucleophiles:: A versatile trigger for assembling oxygen heterocycles [J].

Barluenga, J ;

Vázquez-Villa, H ;

Ballesteros, A ;

González, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (30) :9028-9029

[8] Regioselective synthesis of natural and unnatural (Z)-3-(1-alkylidene)phthalides and 3-substituted isocoumarins starting from methyl 2-hydroxybenzoates [J].

Bellina, F ;

Ciucci, D ;

Vergamini, P ;

Rossi, R .

TETRAHEDRON, 2000, 56 (16) :2533-2545

[9] PALLADIUM-CATALYZED ADDITION OF MALONATE TYPE COMPOUNDS TO ALLENES VIA A HYDROPALLADATION PROCESS [J].

BESSON, L ;

GORE, J ;

GAZES, B .

TETRAHEDRON LETTERS, 1995, 36 (22) :3853-3856

[10] Allenic compounds and isothiocyanates as key building units in the synthesis of heterocycles [J].

Brandsma, L ;

Nedolya, NA .

SYNTHESIS-STUTTGART, 2004, (05) :735-745

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