Directed deprotonation of 7-methyl-1-aminobenzotriazole:: an approach to ortho-substituted benzyne precursors

被引:7
作者
Birkett, MA
Knight, DW
Giles, RG
Mitchell, MB
机构
[1] Univ Nottingham, Dept Chem, Nottingham NG7 2RD, England
[2] SB Pharmaceut, Tonbridge TN11 9AN, Kent, England
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 15期
关键词
D O I
10.1039/a803251c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lateral deprotonation bf N-Boc-1-amino-7-methylbenzotriazole 7 using BuLi-TMEDA leads to the synthetically useful dianion 18, which can be alkylated and which condenses smoothly with a range of aldehydes, ketones and epoxides to provide derivatives (19, 20 and 21 respectively), which are potentially useful in the generation of substituted benzynes.
引用
收藏
页码:2301 / 2305
页数:5
相关论文
共 35 条
[1]  
[Anonymous], [No title captured]
[2]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM BOC DERIVATIVES OF CYCLIC AMINES [J].
BEAK, P ;
LEE, WK .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (05) :1109-1117
[3]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM THE BOC PIPERIDINES [J].
BEAK, P ;
LEE, WK .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2578-2580
[4]   SYNTHESIS OF POLYCYCLICS VIA ARYNE ARYLATION REACTIONS [J].
BIEHL, ER ;
KHANAPURE, SP .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (08) :275-281
[5]   A ROUTE TO ORTHO-SUBSTITUTED BENZYNE PRECURSORS BY DEPROTONATION OF 7-METHYL-1-AMINOBENZOTRIAZOLE DERIVATIVES [J].
BIRKETT, MA ;
KNIGHT, DW ;
MITCHELL, MB .
TETRAHEDRON LETTERS, 1993, 34 (43) :6935-6938
[6]   A NEW APPROACH TO DIHYDROBENZOFURANS BY INTRAMOLECULAR TRAPPING OF BENZYNES BY HYDROXYL FUNCTIONS [J].
BIRKETT, MA ;
KNIGHT, DW ;
MITCHELL, MB .
TETRAHEDRON LETTERS, 1993, 34 (43) :6939-6940
[7]   THE GENERATION AND SYNTHETIC UTILITY OF DIANIONS DERIVED FROM BENZOFURANCARBOXYLIC ACIDS [J].
BUTTERY, CD ;
KNIGHT, DW ;
NOTT, AP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (12) :2839-2843
[8]  
CADOGAN JIG, 1969, J CHEM SOC CHEM COMM, P770
[9]   REACTIVE INTERMEDIATES .I. SYNTHESIS AND OXIDATION OF 1- AND 2-AMINOBENZOTRIAZOLE [J].
CAMPBELL, CD ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05) :742-&
[10]   REACTIVE INTERMEDIATES .2. SOME ADDITION REACTIONS OF BENZYME [J].
CAMPBELL, CD ;
REES, CW .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05) :748-&