Sinteză monotopă

În chimie, sinteza monotopă sau sinteza one-pot[1] este o sinteză chimică în care un reactiv suferă mai multe reacții succesive și/sau simultane într-un singur amestec de reacție (un singur reactor, de exemplu), evitând astfel procesele lungi de separare și purificare a compușilor intermediari. Acest tip de reacție este utilizat des și preferat de către chimiști, deoarece le permite să economisească timp și să crească randamentul chimic total. Procesul prin care o sinteză cu mai multe etape este redusă la o sinteză monotopă se numește telescopare.

Un exemplu de sinteză monotopă este sinteza totală a tropinonei sau sinteza Gassman a indolului.

O sinteză monotopă secvențială este o sinteză în care reactivii sunt adăugați în etape, unul câte unul, fără separare intermediară.

Într-o sinteză de acest tip[2], reacția 3-N-tosilaminofenolului I cu acroleina II produce hidroxichinolină III prin 4 etape secvențiale, fără separarea intermediarilor[3].

Preparat cu o oală de 7-hidroxichinolină
Preparat cu o oală de 7-hidroxichinolină

Referințe

  1. ^ În engleză, literalmente: o sinteză într-un singur recipient
  2. ^ One-Pot Preparation of 7-Hydroxyquinoline, Mark Cameron, R. Scott Hoerrner, James M. McNamara, Margaret Figus, and Scott Thomas; Org. Process Res. Dev., 2006, 10(1), pp. 149-152.
  3. ^ L'addition de l'acroléine (en bleu) est une réaction de Michael catalysée par la [[{{{2}}}|N,N-diisopropylamine]]⁠(en)[traduceți]. La présence d'Éthanol permet la conversion de l'Aldéhyde en Acétal (1b) mais cette réaction est inversée quand de l'Acide chlorhydrique est ajouté au Milieu réactionnel⁠(d) (en rouge). L'Énolate réagit comme un Électrophile dans une Réaction de Friedel-Crafts avec fermeture de cycle. Le groupe alcool est éliminé en présence d'Hydroxyde de potassium via une déshydratation (en vert) et quand dans l'étape finale, le milieu est neutralisé à pH 7 (en rose), le groupe tosyl⁠(d) est aussi éliminé.

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