A practical and versatile method for the synthesis of 2H-pyrrolo [3,4-b]quinolin-9(4H)-one skeleton via tosylmethyl isocyanide (TosMIC) reaction has been developed. Many attempts have been made to reverse the null reactivity of 4-hydroxyquinoline and its N-alkyl derivatives toward TosMIC reactant. For this reason various molecular modifications have been improved for the purpose of obtaining a reactive substrate. tert-Butyl-4-oxoquinoline-1(4H)-carboxylate resulted in the best substrate to provide the desired tricyclic system via facile TosMIC reaction.
CONVENIENT ROUTE TO 2H-PYRROLO [3,4-b]QUINOLIN-9(4H)-ONE SKELETON VIA TOSMIC REACTION / Rosi, Federica; CUZZUCOLI CRUCITTI, Giuliana; Alberto, Iacovo; Gaetano, Miele; Pescatori, Luca; DI SANTO, Roberto; Costi, Roberta. - In: SYNTHETIC COMMUNICATIONS. - ISSN 1532-2432. - STAMPA. - 43:(2013), pp. 1063-1072. [10.1080/00397911.2011.622062]
CONVENIENT ROUTE TO 2H-PYRROLO [3,4-b]QUINOLIN-9(4H)-ONE SKELETON VIA TOSMIC REACTION
ROSI, FEDERICA;CUZZUCOLI CRUCITTI, GIULIANA;PESCATORI, LUCA;DI SANTO, Roberto;COSTI, Roberta
2013
Abstract
A practical and versatile method for the synthesis of 2H-pyrrolo [3,4-b]quinolin-9(4H)-one skeleton via tosylmethyl isocyanide (TosMIC) reaction has been developed. Many attempts have been made to reverse the null reactivity of 4-hydroxyquinoline and its N-alkyl derivatives toward TosMIC reactant. For this reason various molecular modifications have been improved for the purpose of obtaining a reactive substrate. tert-Butyl-4-oxoquinoline-1(4H)-carboxylate resulted in the best substrate to provide the desired tricyclic system via facile TosMIC reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
