NEW SYNTHETIC ROUTES TO FURANS AND DIHYDROFURANS FROM 1-PROPARGYLBENZOTRIAZOLE

被引:36
作者
KATRITZKY, AR
LI, JQ
GORDEEV, MF
机构
[1] Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville
关键词
D O I
10.1021/jo00063a022
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Base-assisted cyclizations of 1-[3-[hydroxy(substituted methyl)]propargyl]benzotriazoles, derived from lithiated 1-propargylbenzotriazole (1) and aromatic aldehydes or ketones, gave 2-arylfurans 5 or 1-(5,5-diaryl-2,5-dihydrofuran-2-yl)benzotriazoles 7, respectively, in high yields. Compounds 7 with Grignard reagents yielded trisubstituted 2,5-dihydrofurans 9.
引用
收藏
页码:3038 / 3041
页数:4
相关论文
共 23 条
[1]   CYCLOREVERSIONS OF ANIONS FROM TETRAHYDROFURANS - CONVENIENT SYNTHESIS OF LITHIUM ENOLATES OF ALDEHYDES [J].
BATES, RB ;
POTTER, DE ;
KROPOSKI, LM .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (04) :560-&
[2]   APPLICATION OF ALLENYLSILANES IN [3 + 2] ANNULATION APPROACHES TO OXYGEN AND NITROGEN-HETEROCYCLES [J].
DANHEISER, RL ;
KWASIGROCH, CA ;
TSAI, YM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (24) :7233-7235
[3]   A NEW SYNTHESIS OF SUBSTITUTED FURANS [J].
DANHEISER, RL ;
STONER, EJ ;
KOYAMA, H ;
YAMASHITA, DS ;
KLADE, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4407-4413
[4]   SCOPE AND STEREOCHEMICAL COURSE OF THE (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION [J].
DANHEISER, RL ;
CARINI, DJ ;
FINK, DM ;
BASAK, A .
TETRAHEDRON, 1983, 39 (06) :935-947
[5]  
DONNELLY DMX, 1984, COMPREHENSIVE HETERO, V3, P705
[6]   FUNCTIONALIZED ORGANOLITHIUM REAGENTS .9. LITHIATION AND ISOMERIZATION OF ALLYLIC AMINES AS A GENERAL-ROUTE TO ENAMINES AND THEIR CARBONYL DERIVATIVES [J].
EISCH, JJ ;
SHAH, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2955-2957
[7]   [2 + 3] AND [3 + 4] ANNULATION OF ENONES - ENANTIOCONTROLLED TOTAL SYNTHESIS OF (-)-RETIGERANIC ACID [J].
HUDLICKY, T ;
FLEMING, A ;
RADESCA, L .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6691-6707
[8]   A NEW [2+3] ANNULATION FOR HIGHLY FUNCTIONALIZED DIHYDROFURANS VIA C-C BOND FORMATION [J].
HUDLICKY, T ;
BARBIERI, G .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (15) :4598-4600
[9]   A SIMPLE ROUTE TO FURANS BY ORGANO-ALUMINUM REAGENTS [J].
ISHIGURO, M ;
IKEDA, N ;
YAMAMOTO, H .
CHEMISTRY LETTERS, 1982, (07) :1029-1030
[10]   AN IMPROVED PROCEDURE FOR THE PREPARATION OF SUBSTITUTED 4-HYDROXY-4,5-DIHYDROFURANS [J].
JAUCH, J ;
SCHURIG, V .
TETRAHEDRON LETTERS, 1991, 32 (36) :4687-4690