2-chlorophenyl zinc bromide: a convenient nucleophile for the mannich-related multicomponent synthesis of clopidogrel and ticlopidine

A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2010-11, Vol.15 (11), p.8144-8155
Hauptverfasser:	Aillaud, Isabelle, Haurena, Caroline, Gall, Erwan Le, Martens, Thierry, Ricci, Gino
Format:	Artikel
Sprache:	eng
Schlagworte:	amino acids Bromides - chemistry cobalt Cobalt - chemistry Molecular Structure multicomponent reactions organozinc reagents Platelet Aggregation Inhibitors - chemical synthesis Platelet Aggregation Inhibitors - chemistry Reagents Ticlopidine - analogs & derivatives Ticlopidine - chemical synthesis Ticlopidine - chemistry zinc Zinc - chemistry Zinc Compounds - chemistry
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Beschreibung
Zusammenfassung:	A methodological study devoted to the Mannich-like multicomponent synthesis of the antiplatelet agent (±)‑clopidogrel (7) and the ethyl ester analogue 6 is described. The process involves the formation of 2-chlorophenyl zinc bromide (2) and its subsequent reaction with an alkyl glyoxylate and 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3). We demonstrate that the organozinc reagent 2 also constitutes a very convenient nucleophile for the multicomponent synthesis of the benzylamine core of ticlopidine (9).
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules15118144