Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3 + 2) Annulation and Aromatization Cascade Reaction of β'-Acetoxy Allenoate and 1,2-Bisnucleophile.
The amine-catalyzed cascade (3 + 2) annulation and aromatization sequence between β'-acetoxy allenoates and 1,2-bisnucleophiles has been developed. When 1,4-dithane-2,5-diol is used as the bisnucleophile partner, the corresponding reaction affords fully substituted thiophene-2-carbaldehyde, which might proceed via the amine-catalyzed (3 + 2) annulation and subsequent oxidative aromatization. The reaction protocol is also applicable to a 2-tosylamino-carbonyl bisnucleophile, wherein the (3 + 2) annulation is followed by 1,2-elimination of a tosyl group and isomerization to give a 1H-pyrrole product.
College of Chemistry and Molecular Engineering, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
Chunjie
C
Ni
College of Chemistry and Molecular Engineering, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.
MingLi
M
Wang
College of Chemistry and Molecular Engineering, East China University of Science and Technology , 130 Meilong Road, Shanghai 200237, China.|Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University , 1 Gehu Road, Changzhou 213164, China.
Xiaofeng
X
Tong