167024-66-0Relevant articles and documents
Facile Access to 1,4-Disubstituted Pyrrolo[1,2- a ]pyrazines from α-Aminoacetonitriles
Basha, Mushkin,Belema, Makonen,Dhar, T. G. Murali,Gupta, Anuradha,Gupta, Arun Kumar,Indasi, Gopi Kumar,Karmakar, Ananta,Mathur, Arvind,Meanwell, Nicholas A.,Ramalingam, Sridharan,Rampulla, Richard
supporting information, p. 441 - 449 (2020/01/23)
An efficient and practical synthetic protocol for the synthesis of 1,4-disubstituted pyrrolo[1,2- a ]pyrazine derivatives is described that originates from α-substituted pyrroloacetonitriles which, in turn, are readily available from aryl and alkyl aldehydes. The α-pyrroloacetonitriles were subjected to a Friedel-Crafts acylation with methyl chlorooxoacetate followed by reduction of the nitrile group under Pd-catalyzed hydrogenation conditions and finally aromatization with DDQ leading to the desired pyrrolo[1,2- a ]pyrazine derivatives. This method was generalized and successfully applied to various aryl, heteroaryl, and alkyl substrates. The developed protocol provides direct and convenient access to 1,4-disubstituted ring systems in moderate to good overall yields (51-68percent) without the need for purification of the intermediates. Further functionalization via the stepwise halogenation (bromination, iodination) and nitration was also demonstrated. In addition, the potential of the ester functionality for elaboration was demonstrated by manipulating into heterocyclic ring systems, exemplified by conversion into benzoxazole derivatives.
Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
Singh, Rahulkumar Rajmani,Liu, Rai-Shung
supporting information, p. 4593 - 4596 (2017/04/28)
Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.
An efficient and scalable synthesis of the spirocyclic glycine transporter inhibitor GSK2137305
Graham, Jonathan P.,Langlade, Nathalie,Northall, John M.,Roberts, Alastair J.,Whitehead, Andrew J.
experimental part, p. 44 - 48 (2011/09/15)
An efficient and scalable synthesis of a glycine transporter inhibitor is presented. The key steps in the synthetic sequence are the formation of a spirocyclic imidazolidinone from an -amino nitrile and a cyclic ketone and an arylation of 4-methyl imidazo