TY - JOUR
T1 - One-Pot Synthesis of Spirotetrahydrooxino[3,4-c]pyridines and Spirotetrahydrofuro[3,2-b]pyridin-2-ones via Lactonization from Activated Pyridyldihydroozaxoles and Bis(trimethylsilyl)ketene Acetals
AU - Gómez-García, Omar
AU - Gómez, Elizabeth
AU - Toscano, Rubén A.
AU - Salgado-Zamora, Héctor
AU - Álvarez-Toledano, Cecilio
N1 - Publisher Copyright:
© Georg Thieme Verlag.
PY - 2016/5/1
Y1 - 2016/5/1
N2 - 5-Methyl-2-(pyridin-3-yl)-4,5-dihydrooxazole and 5-methyl-2-(pyridin-4-yl)-4,5-dihydrooxazole activated by triflic anhydride underwent lactonization with bis(trimethylsilyl)ketene acetals to provide tetrahydrooxino[3,4-c]pyridines and tetrahydrofuro[3,2-b]pyridin-2-ones. Formation of the product was controlled by the position of the pyridyl substituent at C-3 and C-4 of the pyridyldihydrooxazole. On the other hand, 1-(trifluoromethylsulfonamido)propan-2-yl picolinate was obtained under the same conditions from 5-methyl-2-(pyridin-2-yl)-4,5-dihydrooxazole.
AB - 5-Methyl-2-(pyridin-3-yl)-4,5-dihydrooxazole and 5-methyl-2-(pyridin-4-yl)-4,5-dihydrooxazole activated by triflic anhydride underwent lactonization with bis(trimethylsilyl)ketene acetals to provide tetrahydrooxino[3,4-c]pyridines and tetrahydrofuro[3,2-b]pyridin-2-ones. Formation of the product was controlled by the position of the pyridyl substituent at C-3 and C-4 of the pyridyldihydrooxazole. On the other hand, 1-(trifluoromethylsulfonamido)propan-2-yl picolinate was obtained under the same conditions from 5-methyl-2-(pyridin-2-yl)-4,5-dihydrooxazole.
KW - ketene acetals
KW - lactonization
KW - pyridyldihydrooxazoles
KW - spirotetrahydrofuro[3,2-b]pyridin-2-ones
KW - spirotetrahydrooxino[3,4,-c]pyridines
UR - http://www.scopus.com/inward/record.url?scp=84960153546&partnerID=8YFLogxK
U2 - 10.1055/s-0035-1560422
DO - 10.1055/s-0035-1560422
M3 - Artículo
SN - 0039-7881
VL - 48
SP - 1371
EP - 1380
JO - Synthesis (Germany)
JF - Synthesis (Germany)
IS - 9
ER -