Domino Synthesis of 2‑Substituted Benzothiazoles by Base-Promoted Intramolecular C–S Bond Formation
journal contributionposted on 16.09.2019, 17:38 authored by Yogendra Kumar, Hiriyakkanavar Ila
A new, transition-metal-free, domino synthesis of 2-substituted benzothiazoles has been developed, involving base-promoted one-pot addition of active methylene compounds to o-iodoarylisothioacyanates and subsequent intramolecular C–S bond formation of the resulting thioamidate anion. The reaction proceeds at room temperature within 1–3 h, affording diversely substituted benzothiazoles in high yields. A possible radical intermediate pathway, via an SRN1 mechanism, has been proposed for intramolecular C–S bond formation.
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diverselymethylene compoundspathwayintramolecularthioamidate anionBenzothiazoledomino synthesisS RN 1 mechanismbase-promoted one-pot additionSubstitutedFormation2-domino Synthesisreaction proceedsBase-Promotediodoarylisothioacyanateformationtransition-metal-freeBondyieldbenzothiazoleroom temperatureIntramolecularbond