91374-22-0Relevant articles and documents
Comprehensive Study of the Organic-Solvent-Free CDI-Mediated Acylation of Various Nucleophiles by Mechanochemistry
Mtro, Thomas-Xavier,Bonnamour, Julien,Reidon, Thomas,Duprez, Anthony,Sarpoulet, Jordi,Martinez, Jean,Lamaty, Frdric
supporting information, p. 12787 - 12796 (2015/09/01)
Acylation reactions are ubiquitous in the synthesis of natural products and biologically active compounds. Unfortunately, these reactions often require the use of large quantities of volatile and/or toxic solvents, either for the reaction, purification or isolation of the products. Herein we describe and discuss the possibility of completely eliminating the use of organic solvents for the synthesis, purification and isolation of products resulting from the acylation of amines and other nucleophiles. Thus, utilisation of N,N′-carbonyldiimidazole (CDI) allows efficient coupling between carboxylic acids and various nucleophiles under solvent-free mechanical agitation, and water-assisted grinding enables both the purification and isolation of pure products. Critical parameters such as the physical state and water solubility of the products, milling material, type of agitation (vibratory or planetary) as well as contamination from wear are analysed and discussed. In addition, original organic-solvent-free conditions are proposed to overcome the limitations of this approach. The calculations of various green metrics are included, highlighting the particularly low environmental impact of this strategy.
Syntheses and in Vitro Evaluation of 4-(2-Aminoethyl)-2(3H)-indolones and Related Compounds as Peripheral Prejunctional Dopamine Receptor Agonists
DeMarinis, Robert M.,Gallagher, Gregory,Hall, Ralph F.,Franz, Robert G.,Webster, Charles,et al.
, p. 939 - 947 (2007/10/02)
A series of (β-aminoethyl)indolones and related compounds was synthesized and evaluated in vitro as peripheral prejunctional dopaminergic agonists in the field-stimulated isolated perfused rabbit ear artery. 4--7-hydroxy-2(3H)-indolone (26) was the most potent compound (ED50 = 2 +/- 0.3 nM) tested, while the related secondary amine 24 and the des-OH derivatives 28 and 34 were only slightly less potent. 4-Methoxy-benzeneethanamine and 2-methyl-3-nitrophenylacetic acid were employed as starting materials for the synthesis of the 4-(β-aminoethyl)indolones.The ring-opened 3-acylamino analogues 46 and 47 were prepared via nitration of the phenethylamine 43 derived from 4-methoxyphenylacetic acid.The inactive isomeric indolones 38, 39, and 41 were derived from 4-nitrobenzeneethanamine and from indolone-6-acetic acid (13).
4--2(3H)-indolone: A Prejunctional Dopamine Receptor Agonist
Gallagher, Gregory,Lavanchy, Patricia G.,Wilson, James W.,Hieble, J. Paul,DeMarinis, Robert M.
, p. 1533 - 1536 (2007/10/02)
4--2(3H)-indolone (1c) (SK and F 101468) is a potent and selective prejunctional dopamine receptor agonist.It caused a dose-related inhibition of the constrictor response to electrical stimulation in the isolated perfused rabbit ear artery (EC50 = 100 nM), and this response was antagonized by (S)-sulpiride (KB = 7 nM).Compound 1c did not stimulate or block dopamine-sensitive adenylate cyclase and did not produce stimulation of the central nervous system in rats.It was prepared from (2-methyl-3-nitrophenyl)acetic acid in a multistep sequence based on the Reissert indole synthesis.