Facile preparation of various heteroaromatic compounds via azatitanacyclopentadiene intermediates

被引:75
作者
Suzuki, D
Nobe, Y
Watai, Y
Tanaka, R
Takayama, Y
Sato, F
Urabe, H
机构
[1] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
[2] Tokyo Inst Technol, Grad Sch Biosci & Biotechnol, Dept Biol Informat, Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
D O I
10.1021/ja0502730
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Coupling of acetylene, nitrile, and a titanium reagent, Ti(O-i-Pr)(4)/2 i-PrMgCl, generated new azatitanacyclopentadienes in a highly regioselective manner. Their subsequent reaction with sulfonylacetylene afforded pyridyltitanium compounds, which, upon reaction with electrophiles, gave substituted pyridines virtually as a single isomer. When optically active nitriles were used in this reaction, chiral pyridines were obtained without loss of the enantiopurity. Alternatively, the azatitanacyclopentadiene prepared from an unsymmetrical acetylene reacted with an aldehyde or another nitrile to give furans or pyrroles having four different substituents again in a regioselective manner.
引用
收藏
页码:7474 / 7479
页数:6
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共 71 条
[1]  
[Anonymous], 1984, COMPREHENSIVE HETERO
[2]   Ti(II)-mediated conversion of α-heterosubstituted (O, N, S) nitriles to functionalized cyclopropylamines.: Effect of chelation on the cyclopropanation step [J].
Bertus, P ;
Szymoniak, J .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (11) :3965-3968
[3]   COUPLING OF 2 ETHYNE MOLECULES AT RHODIUM VERSUS COUPLING OF 2 RHODIUM ATOMS AT ETHYNE .2. IMPLICATIONS FOR THE REACTIVITY - CATALYTIC AND STOICHIOMETRIC FUNCTIONALIZATION REACTIONS OF ETHYNE [J].
BIANCHINI, C ;
MELI, A ;
PERUZZINI, M ;
VACCA, A ;
VIZZA, F .
ORGANOMETALLICS, 1991, 10 (03) :645-651
[4]   ORGANOCOBALT COMPOUNDS IN THE SYNTHESIS OF PYRIDINES - AN EXAMPLE OF STRUCTURE-EFFECTIVITY RELATIONSHIPS IN HOMOGENEOUS CATALYSIS [J].
BONNEMANN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04) :248-262
[5]  
BONNEMANN H, 1998, TRANSITION METALS OR, V1, P114
[6]   A new method for the preparation of alkynes from vinyl triflates. [J].
Brummond, KM ;
Gesenberg, KD ;
Kent, JL ;
Kerekes, AD .
TETRAHEDRON LETTERS, 1998, 39 (47) :8613-8616
[7]   GROUP-4 METAL-COMPLEXES OF BENZYNES, CYCLOALKYNES, ACYCLIC ALKYNES, AND ALKENES [J].
BUCHWALD, SL ;
NIELSEN, RB .
CHEMICAL REVIEWS, 1988, 88 (07) :1047-1058
[8]   SYNTHESIS OF SUBSTITUTED PYRROLES VIA ZIRCONOCENE COMPLEXES OF IMINES [J].
BUCHWALD, SL ;
WANNAMAKER, MW ;
WATSON, BT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (02) :776-777
[9]  
Caputo R, 1991, COMPREHENSIVE ORGANI, P139
[10]   TETRAHEDRON - ASYMMETRY REPORT NUMBER-16 - SYNTHESIS OF CHIRAL PYRIDINES BY COBALT(I)-CATALYZED COCYCLOTRIMERIZATION OF ACETYLENE WITH OPTICALLY-ACTIVE NITRILES [J].
CHELUCCI, G .
TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :811-826