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Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions).

ABSTRACT: We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as "masked" 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity.

SUBMITTER: Kruithof A

PROVIDER: S-EPMC6154663 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions).

Kruithof Art A Vande Velde Christophe M L CM Ruijter Eelco E Orru Romano V A RV

Molecules (Basel, Switzerland) 20170328 4

We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2<i>H</i>-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as "masked" 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity. ...[more]

PMID: 28350361

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