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Title: Base-Catalyzed Phenol-Mannich Condensation of Preformed Cesium Iminodiacetate. The Direct Synthesis of Calcein Blue AM and Related Acyloxymethyl Esters
A rapid and highly practical one-flask procedure for the positionally selective preparation of (acyloxy)methyl N-(2- hydroxybenzyl)iminodiacetate and related diesters from iminodiacetic acid and phenols is described. The key to this multicomponent phenol-Mannich condensation resides in the use of cesium iminodiacetate as the reaction partner. This protocol has been applied in an unusually direct synthesis of the intracellular fluorescent dye Calcein blue AM, for which scant experimental and spectroscopic data are presently available.  more » « less
Award ID(s):
2018388
PAR ID:
10482197
Author(s) / Creator(s):
;
Publisher / Repository:
ACS
Date Published:
Journal Name:
The Journal of Organic Chemistry
Volume:
88
Issue:
16
ISSN:
0022-3263
Page Range / eLocation ID:
12064 to 12068
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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