Synthesis of Potentially β-Blocking Practolol Derivatives: (E +Z)-3-[4-(3-Iodoprop-2-enyloxycarbonylamino)phenoxy]-1-(isopropylamino)propan-2-ol

Autor:	Pierre-Marc Léo, Marcel Apparu, Younes Ben Tiba, Daniel Fagret
Rok vydání:	2000
Předmět:	Reaction conditions chemistry.chemical_compound Carbamate chemistry medicine.medical_treatment Organic Chemistry medicine Amine gas treating Chloroformate Physical and Theoretical Chemistry Medicinal chemistry Practolol medicine.drug
Zdroj:	European Journal of Organic Chemistry. 2000:1007-1012
ISSN:	1099-0690 1434-193X
DOI:	10.1002/(sici)1099-0690(200003)2000:6<1007::aid-ejoc1007>3.0.co;2-i
Popis:	The iodinatied carbamates 3 (E + Z), with potential β-blocking properties, were synthesized. The first route chosen, from 4-aminophenol and the chloroformate β7, had to be abandoned because of the formation of the oxazolidinone 10 during the epoxidation step. The aminoalcohol 17 prepared from the practolol 1 finally gave the target compounds by condensation with the iodoallylic chloroformates 8 (E + Z). The secondary Boc-protected amine function was regenerated without removing the carbamate function situated in the p-postion, by using mild reaction conditions (1 N HCl).
Databáze:	OpenAIRE
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