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

O Petrovskaia; B M Taylor; D B Hauze; P J Carroll; M M Joullié

doi:10.1021/jo0105179

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

J Org Chem. 2001 Nov 16;66(23):7666-75. doi: 10.1021/jo0105179.

Authors

O Petrovskaia¹, B M Taylor, D B Hauze, P J Carroll, M M Joullié

Affiliation

¹ Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104-6323, USA.

PMID: 11701019
DOI: 10.1021/jo0105179

Abstract

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.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Amino Acids / chemistry*
Indans / chemistry*
Pyrrolidines / chemistry
Spiro Compounds / chemistry

Substances

1,2-indanedione
Amino Acids
Indans
Pyrrolidines
Spiro Compounds

Grants and funding

CA-40081/CA/NCI NIH HHS/United States