Thiocarbonyl induced heterocumulenic Pauson-Khand type reaction:: expedient synthetic method for thieno[2,3-b] indol-2-ones

被引：35

作者：

Saito, Takao ^{[1
]}

Nihei, Hiroshi ^{[1
]}

Otani, Takashi ^{[1
]}

Suyama, Toshiyuki ^{[1
]}

Furukawa, Naoki ^{[1
]}

Saito, Masatoshi ^{[1
]}

机构：

[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Shinjuku Ku, Tokyo 162, Japan

来源：

CHEMICAL COMMUNICATIONS | 2008年 / 02期

关键词：

D O I：

10.1039/b712739a

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first examples of C L S induced Pauson-Khand type reactions are described; 2-alkynylphenyl isothiocyanates were converted to 3-substituted-2H-thieno[2,3-b]indol-2-ones in the presence of a stoichiometric amount of Mo(CO)(6) or Co-2(CO)(8), or a catalytic amount of Rh catalyst under an atmospheric pressure of carbon monoxide.

引用

页码：172 / 174

页数：3

共 59 条

[1] Butenolide synthesis by molybdenum-mediated hetero-Pauson-Khand reaction of alkynyl aldehydes [J].

Adrio, Javier ;

Carretero, Juan C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (04) :778-779

[2] PAUSON-KHAND REACTION WITH ALLENIC COMPOUNDS .1. SYNTHESIS OF 4-ALKYLIDENE-2-CYCLOPENTENONES [J].

AHMAR, M ;

ANTRAS, F ;

CAZES, B .

TETRAHEDRON LETTERS, 1995, 36 (25) :4417-4420

[3] Cascade radical reactions via α-(arylsulfanyl)imidoyl radicals:: Competitive [4+2] and [4+1] radical annulations of alkynyl isothiocyanates with aryl radicals [J].

Benati, L ;

Calestani, G ;

Leardini, R ;

Minozzi, M ;

Nanni, D ;

Spagnolo, P ;

Strazzari, S ;

Zanardi, G .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09) :3454-3464

[4] TITANOCENE-CATALYZED CONVERSION OF ENYNES TO BICYCLIC CYCLOPENTENONES [J].

BERK, SC ;

GROSSMAN, RB ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (11) :4912-4913

[5] The Pauson-Khand reaction, a powerful synthetic tool for the synthesis of complex molecules [J].

Blanco-Urgoiti, J ;

Añorbe, L ;

Pérez-Serrano, L ;

Domínguez, G ;

Pérez-Castells, J .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (01) :32-42

[6] When the Pauson-Khand and Pauson-Khand type reactions go awry:: a plethora of unexpected results [J].

Boñaga, LVR ;

Krafft, ME .

TETRAHEDRON, 2004, 60 (44) :9795-9833

[7] Ru3(CO)12-catalyzed cyclocarbonylation of yne-aldehydes to bicyclic α,β-unsaturated γ-butyrolactones [J].

Chatani, N ;

Morimoto, T ;

Fukumoto, Y ;

Murai, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (21) :5335-5336

[8] PROMOTERS FOR THE (ALKYNE)HEXACARBONYLDICOBALT-BASED CYCLOPENTENONE SYNTHESIS [J].

CHUNG, YK ;

LEE, BY ;

JEONG, N ;

HUDECEK, M ;

PAUSON, PL .

ORGANOMETALLICS, 1993, 12 (01) :220-223

[9] Direct synthesis of fused, bicyclic gamma-butyrolactones via tandem reductive cyclization-carbonylation of tethered enals and enones [J].

Crowe, WE ;

Vu, AT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (06) :1557-1558

[10] Synthesis of thienodolin [J].

Engqvist, R ;

Javaid, A ;

Bergman, J .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) :2589-2592

← 1 2 3 4 5 6 →