TY - JOUR
T1 - Conjugate systems in the construction of heterocycles and quaternary stereocenters
AU - González-Romero, Carlos
AU - Bernal, Pablo
AU - Jiménez, Fabiola
AU - Cruz, María Del Carmen
AU - Fuentes-Benites, Aydeé
AU - Benavides, Adriana
AU - Bautista, Rafael
AU - Tamariz, Joaquín
N1 - Funding Information:
We are grateful to Drs. Hugo A. Jiménez-Vázquez, Francisco Delgado, Gerardo Zepeda, and Francisco Díaz for their assistance and interesting comments, as well as to Dr. Eusebio Juaristi for some laboratory facilities. J.T. acknowledges DEPI/IPN (Grants 20030147, 20040123, 20050151, and 20060583) and CONACYT (Grants 32273-E and 43508-Q) for financial support. C.G.-R. and A.F.-B. thank Universidad Autónoma del Estado de México for its financial support, and P.B., F.J., M.C.C., A.B., and R.B. thank CONACYT for scholarships awarded. R.B. thanks Ludwig K. Hellweg Foundation for a scholarship complement. J.T. is a fellow of the EDI-IPN and COFAA-IPN programs.
PY - 2007/2
Y1 - 2007/2
N2 - The synthetic application of 4,5-bis-alkylidene-1,3-oxazolidin-2-ones led to the efficient and regioselective synthesis of 2-(3H)-benzoxazolones and diarylamines with a short methodology. They were also valuable synthons in a total synthesis of naturally occurring carbazoles. New enantiopure 4-oxazoline-2-one and 4-methylene-2-oxazolidinone were prepared via a one-pot microwave (MW)-promoted condensation of α-ketols and an enantiopure isocyanate. These enamides were efficient nucleophiles when added to Michael acceptors to give a series of compounds with quaternary stereocenters in fairly good stereoisomeric ratios. The novel approach for the synthesis of benzofurans and indoles by intramolecular cyclization of enaminones has been applied in the preparation of furobenzofurans starting from benzo-bis-enaminones.
AB - The synthetic application of 4,5-bis-alkylidene-1,3-oxazolidin-2-ones led to the efficient and regioselective synthesis of 2-(3H)-benzoxazolones and diarylamines with a short methodology. They were also valuable synthons in a total synthesis of naturally occurring carbazoles. New enantiopure 4-oxazoline-2-one and 4-methylene-2-oxazolidinone were prepared via a one-pot microwave (MW)-promoted condensation of α-ketols and an enantiopure isocyanate. These enamides were efficient nucleophiles when added to Michael acceptors to give a series of compounds with quaternary stereocenters in fairly good stereoisomeric ratios. The novel approach for the synthesis of benzofurans and indoles by intramolecular cyclization of enaminones has been applied in the preparation of furobenzofurans starting from benzo-bis-enaminones.
KW - 4,5-dimethylene-2-oxazolidinone dienes
KW - 4-oxazolin-2-ones
KW - Carbazoles
KW - Enaminones
KW - Furobenzofurans
UR - http://www.scopus.com/inward/record.url?scp=33846906940&partnerID=8YFLogxK
U2 - 10.1351/pac200779020181
DO - 10.1351/pac200779020181
M3 - Artículo
AN - SCOPUS:33846906940
SN - 0033-4545
VL - 79
SP - 181
EP - 191
JO - Pure and Applied Chemistry
JF - Pure and Applied Chemistry
IS - 2
ER -