Abstract
The paper describes a mild, selective, and rapid replacement of an N-methyl group of tertiary amines with other alkyl groups via a simple one-pot procedure. This transformation is easily achieved by preparation of the appropriate quaternary ammonium salt in sulfolane and in situ treatment with sodium sulfide or potassium thioacetate. The protocol is successfully applied to the transformation of dihydrolysergol, dextromethorphan and laudanosine (as models of ergot and opium N-methyl alkaloids) into various N-alkyl congeners.
| Original language | English |
|---|---|
| Pages (from-to) | 2398-2403 |
| Number of pages | 6 |
| Journal | Journal of the Chemical Society. Perkin Transactions 1 |
| Issue number | 19 |
| Publication status | Published - 2001 |
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ASJC Scopus subject areas
- Chemistry(all)
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Simple and selective one-pot replacement of the N-methyl group of tertiary amines by quaternization and demethylation with sodium sulfide or potassium thioacetate : An application to the synthesis of pergolide. / Anastasia, L.; Cighetti, G.; Allevi, P.
In: Journal of the Chemical Society. Perkin Transactions 1, No. 19, 2001, p. 2398-2403.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Simple and selective one-pot replacement of the N-methyl group of tertiary amines by quaternization and demethylation with sodium sulfide or potassium thioacetate
T2 - An application to the synthesis of pergolide
AU - Anastasia, L.
AU - Cighetti, G.
AU - Allevi, P.
PY - 2001
Y1 - 2001
N2 - The paper describes a mild, selective, and rapid replacement of an N-methyl group of tertiary amines with other alkyl groups via a simple one-pot procedure. This transformation is easily achieved by preparation of the appropriate quaternary ammonium salt in sulfolane and in situ treatment with sodium sulfide or potassium thioacetate. The protocol is successfully applied to the transformation of dihydrolysergol, dextromethorphan and laudanosine (as models of ergot and opium N-methyl alkaloids) into various N-alkyl congeners.
AB - The paper describes a mild, selective, and rapid replacement of an N-methyl group of tertiary amines with other alkyl groups via a simple one-pot procedure. This transformation is easily achieved by preparation of the appropriate quaternary ammonium salt in sulfolane and in situ treatment with sodium sulfide or potassium thioacetate. The protocol is successfully applied to the transformation of dihydrolysergol, dextromethorphan and laudanosine (as models of ergot and opium N-methyl alkaloids) into various N-alkyl congeners.
UR - http://www.scopus.com/inward/record.url?scp=0034740847&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0034740847&partnerID=8YFLogxK
M3 - Article
SP - 2398
EP - 2403
JO - Journal of the Chemical Society. Perkin Transactions 1
JF - Journal of the Chemical Society. Perkin Transactions 1
SN - 1472-7781
IS - 19
ER -