Efficient base-catalyzed 5-exo-dig cyclization of carbonyl groups on unactivated alkynyl-quinolines:: An entry to versatile oxygenated heterocycles related to the furoquinoline alkaloids family

被引：34

作者：

Godet, T ^{[1
]}

Bosson, J ^{[1
]}

Belmont, P ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5181, F-69622 Villeurbanne, France

来源：

SYNLETT | 2005年 / 18期

关键词：

quinoline; 5-exo-dig cyclization; 1,3-dihydrofuro[3,4-b]quinoline; base-catalyzed cyclization;

D O I：

10.1005/s-2005-918953

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient 5-exo-dig cyclization was observed when TMS-protected alkynyl-quinolines bearing a carbonyl group were submitted to a mixture of an alcohol (alkyl-OH, diol, amino alcohol) with an inorganic base (K2CO3). The cyclization process seems to go through the deprotection of the TMS group prior to the cyclization step. The dihydrofuroquinoline derivatives formed are structurally related to the well-known furoquinoline alkaloids family. The scope and limitations of this reaction have also been studied with diverse bases and various alkynyl and carbonyl derivatives.

引用

页码：2786 / 2790

页数：5

共 41 条

[1] Intramolecular cyclization of δ-iminoacetylenes:: A new entry to pyrazino[1,2-a]indoles [J].

Abbiati, G ;

Arcadi, A ;

Bellinazzi, A ;

Beccalli, E ;

Rossi, E ;

Zanzola, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4088-4095

[2] Novel intramolecular cyclization of N-alkynyl heterocycles containing proximate nucleophiles [J].

Abbiati, G ;

Arcadi, A ;

Beccalli, E ;

Rossi, E .

TETRAHEDRON LETTERS, 2003, 44 (28) :5331-5334

[3] Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].

Alonso, F ;

Beletskaya, IP ;

Yus, M .

CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159

[4] Highly efficient access to strained bicyclic ketals via gold-catalyzed cycloisomerization of bis-homopropargylic diols [J].

Antoniotti, S ;

Genin, E ;

Michelet, V ;

Genêt, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9976-9977

[5] 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

[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] Cyclisations involving attack of carbo- and heteronucleophiles on carbon-carbon π-bonds activated by organopalladium complexes [J].

Balme, G ;

Bouyssi, D ;

Lomberget, T ;

Monteiro, N .

SYNTHESIS-STUTTGART, 2003, (14) :2115-2134

[8] Synthesis of indoles upon sequential reaction of 3-alkynylpyrrole-2-carboxaldehydes with iodonium ions and alkenes.: Preparation of related benzofuran and benzothiophene derivatives [J].

Barluenga, J ;

Vázquez-Villa, H ;

Ballesteros, A ;

González, JM .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (04) :526-530

[9] 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

[10] 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

← 1 2 3 4 5 →