Hydroxy- and Aminopyrroles and Related Compounds

doi:10.1016/b978-0-12-389840-1.50014-0

The Chemistry of Pyrroles

1977

DOI: 10.1016/b978-0-12-389840-1.50014-0

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Hydroxy- and Aminopyrroles and Related Compounds

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2020

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2‐Amino‐5‐(cyanomethylsulfanyl)‐1H‐pyrroles from Propargylamines, Isothiocyanates, and Bromoacetonitrile by One‐Pot Synthetic Protocol

et al. 2020

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Tertiary propargylamines (such as N,N-dialkylpropargylamines, N-propargylpyrrolidine, -piperidine, and -morpholine), isothiocyanates, and bromoacetonitrile have been shown to be readily available building blocks for the highly selective one-pot construction of rare-functionalized pyrroles, namely so far inaccessible 1-substituted 2-amino-5-(cyanomethylsulfanyl)-1Hpyrroles, in up to 92 % yield. This highly efficient and operationally simple approach includes the initial formation of lithium but-2-ynimidothioate (adduct of monolithiated propargylamine and isothiocyanate), its transformation into potassium buta-2,3dienimidothioate under the action of the t-BuOK/DMSO system (through acetylene-allene isomerization and the exchange by cations), intramolecular cyclization into potassium thienylamide (at � 15°C), followed by its re-cyclization into potassium pyrrolylsulfide at a higher temperature (45-60°C), and the final S-alkylation of the latter with bromoacetonitrile. The total reaction time is 45-60 min.[a] Dr. Scheme 4. Plausible mechanism of pyrrole ring construction from propargylamines 1 and isothiocyanates.Scheme 5. Reaction products obtained from lithiated propargylamine 1 b and 2-(vinyloxy)ethyl isothiocyanate by procedure A. Scheme 6. Plausible mechanism of dipyrromethane 5 formation during synthesis of pyrrole 4 i from propargylamine 1 b and 2-(vinyloxy)ethyl isothiocyanate.

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2‐Amino‐5‐(cyanomethylsulfanyl)‐1H‐pyrroles from Propargylamines, Isothiocyanates, and Bromoacetonitrile by One‐Pot Synthetic Protocol

et al. 2020

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Hydroxy- and Aminopyrroles and Related Compounds

Cited by 1 publication

References 171 publications

2‐Amino‐5‐(cyanomethylsulfanyl)‐1H‐pyrroles from Propargylamines, Isothiocyanates, and Bromoacetonitrile by One‐Pot Synthetic Protocol

2‐Amino‐5‐(cyanomethylsulfanyl)‐1H‐pyrroles from Propargylamines, Isothiocyanates, and Bromoacetonitrile by One‐Pot Synthetic Protocol

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