Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3 + 2) Annulation and Aromatization Cascade Reaction of β'-Acetoxy Allenoate and 1,2-Bisnucleophile.

doi:10.1021/acs.orglett.6b00874

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Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3 + 2) Annulation and Aromatization Cascade Reaction of β'-Acetoxy Allenoate and 1,2-Bisnucleophile.

Published Apr 26, 2016 · Chunjie Ni, Mingli Wang, Xiaofeng Tong

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Abstract

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.

Study Snapshot

The amine-catalyzed cascade (3 + 2) annulation and aromatization sequence allows for the synthesis of fully substituted thiophene-2-carbaldehyde and 1H-pyrrole from '-acetoxy allenoates and 1,2-bisnucleophile

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Access to Thiophene and 1H-Pyrrole via Amine-Initiated (3 + 2) Annulation and Aromatization Cascade Reaction of β'-Acetoxy Allenoate and 1,2-Bisnucleophile.

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