TY - JOUR
T1 - Synthesis and reactivity of some thiochroman-3,4-diones.
AU - Gabbutt, Christopher D.
AU - Hepworth, John D.
AU - Heron, B. Mark
PY - 1994/1/1
Y1 - 1994/1/1
N2 - Thiochroman-3,4-diones, which result from the reaction of thiochroman-4-ones with isoamyl nitrite, form fused heterocycles on reaction with 1,2-diamines and with p-anisaldehyde and ammonium acetate. Cyclopenta-[c][1]benzothiopyran-2-one, formed on reaction with dibenzyl ketone, yields a dibenzo[bd]thiopyran after cycloaddition of DMAD. With methyl magnesium iodide, a mixture of thiochroman-3-and 4-ols is fomed which was separated only after the selective dehydration of the 4-ol. The resulting 4-methylene derivative was isolated as the hetero Diels-Alder spiro-liked adduct.
AB - Thiochroman-3,4-diones, which result from the reaction of thiochroman-4-ones with isoamyl nitrite, form fused heterocycles on reaction with 1,2-diamines and with p-anisaldehyde and ammonium acetate. Cyclopenta-[c][1]benzothiopyran-2-one, formed on reaction with dibenzyl ketone, yields a dibenzo[bd]thiopyran after cycloaddition of DMAD. With methyl magnesium iodide, a mixture of thiochroman-3-and 4-ols is fomed which was separated only after the selective dehydration of the 4-ol. The resulting 4-methylene derivative was isolated as the hetero Diels-Alder spiro-liked adduct.
UR - http://www.scopus.com/inward/record.url?scp=0028303579&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)85270-4
DO - 10.1016/S0040-4020(01)85270-4
M3 - Article
AN - SCOPUS:0028303579
VL - 50
SP - 7865
EP - 7878
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 26
ER -