TY - JOUR
T1 - Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine
AU - Barrera, Edson
AU - Hernández-Benitez, R. Israel
AU - González-González, Carlos A.
AU - Escalante, Carlos H.
AU - Fuentes-Benítes, Aydeé
AU - González-Romero, Carlos
AU - Becerra-Martínez, Elvia
AU - Delgado, Francisco
AU - Tamariz, Joaquín
N1 - Publisher Copyright:
© 2022 Wiley-VCH GmbH.
PY - 2022/6/27
Y1 - 2022/6/27
N2 - New and efficient strategies for the conversion of 4-oxazolin-2-ones into 1-methyl and 1,4-dimethyl 3-formylcarbazoles are herein described. Highly convergent cascade and one-pot processes afforded the corresponding diarylamines, as in situ formed synthetic intermediates or final products in high overall yields. Special attention was given to the synthesis of methylated carbazoles by reacting 4,5-dimethyl-4-oxazolin-2-ones with enones under microwave irradiation. The carbazole scaffold was provided by the palladium(II)-catalyzed double C−H activation to generate oxidative cyclization of diarylamines. This methodology allowed for formal total syntheses of four naturally occurring pyrido[4,3-b]carbazole alkaloids ellipticine, 9-methoxyellipticine, olivacine, and 9-methoxyolivacine.
AB - New and efficient strategies for the conversion of 4-oxazolin-2-ones into 1-methyl and 1,4-dimethyl 3-formylcarbazoles are herein described. Highly convergent cascade and one-pot processes afforded the corresponding diarylamines, as in situ formed synthetic intermediates or final products in high overall yields. Special attention was given to the synthesis of methylated carbazoles by reacting 4,5-dimethyl-4-oxazolin-2-ones with enones under microwave irradiation. The carbazole scaffold was provided by the palladium(II)-catalyzed double C−H activation to generate oxidative cyclization of diarylamines. This methodology allowed for formal total syntheses of four naturally occurring pyrido[4,3-b]carbazole alkaloids ellipticine, 9-methoxyellipticine, olivacine, and 9-methoxyolivacine.
KW - 4-Oxazolin-2-ones
KW - Ellipticine
KW - Methylcarbazoles
KW - Microwave chemistry
KW - Palladium
UR - http://www.scopus.com/inward/record.url?scp=85132928132&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202200364
DO - 10.1002/ejoc.202200364
M3 - Artículo
AN - SCOPUS:85132928132
SN - 1434-193X
VL - 2022
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 24
M1 - e202200364
ER -