Investigations of the reaction mechanisms of 1,2-indanediones with amino acids

被引:33
作者
Petrovskaia, O [1 ]
Taylor, BM [1 ]
Hauze, DB [1 ]
Carroll, PJ [1 ]
Joullié, MM [1 ]
机构
[1] Univ Penn, Dept Chem, Philadelphia, PA 19104 USA
关键词
D O I
10.1021/jo0105179
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction mechanisms of amino acids with a new class of fluorogenic reagents were investigated. The structures of colored and fluorescent species formed in these reactions were partially confirmed by experimental evidence. Reaction intermediates, C-N-C 1,3-dipoles derived from imines, were trapped with dipolarophiles in 3 + 2 cycloadditions to form spiropyrrolidines.
引用
收藏
页码:7666 / 7675
页数:10
相关论文
共 28 条
[1]   IMINIUM ION ROUTE TO AZOMETHINE YLIDES FROM PRIMARY AND SECONDARY-AMINES [J].
ARDILL, H ;
GRIGG, R ;
SRIDHARAN, V ;
SURENDRAKUMAR, S ;
THIANPATANAGUL, S ;
KANAJUN, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (08) :602-604
[2]  
BREUR B, 1996, PRAX NATURWISS CHEM, V45, P18
[3]   INTRAMOLECULAR FRIEDEL-CRAFTS ACYLATION OF N-PHTHALOYL-SUBSTITUTED ARYLALANYL AND HOMOPHENYLALANYL CHLORIDES [J].
EFFENBERGER, F ;
STEEGMULLER, D ;
NULL, V ;
ZIEGLER, T .
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (01) :125-130
[4]  
FATIADI AJ, 1978, SYNTHESIS-STUTTGART, P165
[5]   STOICHIOMETRY OF FORMATION OF RUHEMANNS PURPLE IN NINHYDRIN REACTION [J].
FRIEDMAN, M ;
WILLIAMS, LD .
BIOORGANIC CHEMISTRY, 1974, 3 (03) :267-280
[6]   CYCLOADDITION REACTIONS RELEVANT TO THE MECHANISM OF THE NINHYDRIN REACTION - X-RAY CRYSTAL-STRUCTURE OF PROTONATED RUHEMANNS PURPLE, A STABLE 1,3-DIPOLE [J].
GRIGG, R ;
MALONE, JF ;
MONGKOLAUSSAVARATANA, T ;
THIANPATANAGUL, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (05) :421-422
[7]   1,8-DIAZAFLUORENONE AND RELATED-COMPOUNDS - A NEW REAGENT FOR THE DETECTION OF ALPHA-AMINO-ACIDS AND LATENT FINGERPRINTS [J].
GRIGG, R ;
MONGKOLAUSSAVARATANA, T ;
POUNDS, CA ;
SIVAGNANAM, S .
TETRAHEDRON LETTERS, 1990, 31 (49) :7215-7218
[9]  
Grigg R., 1993, ADV CYCLOADDITION, V3, P161
[10]  
Hauze DB, 1998, J FORENSIC SCI, V43, P744