- Synthesis of pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates via the Hurd-Mori reaction. Investigating the effect of the N-protecting group on the cyclization
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A route to methyl pyrrolo[2,3-d][1,2,3]thiadiazole-6-carboxylates as potential plant activators and inducers of systemic acquired resistance (SAR) is reported. A synthetic strategy based on cyclization of the thiadiazole ring system utilizing thionyl chloride via the Hurd-Mori protocol as key step was developed. Success of the ring closure reaction turned out to be highly dependent on the nature of the N-protecting group of the pyrrolidine precursor. While electron donors such as alkyl gave only poor conversion to the required 1,2,3-thiadiazoles, an electron withdrawing substituent such as methyl carbamate gave superior yields.
- Stanetty, Peter,Turner, Martin,Mihovilovic, Marko D.
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p. 367 - 375
(2007/10/03)
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- Δ1 -Pyrroline thiolactim ethers and a process for their preparation
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The present invention relates to Δ1 -pyrroline thiolactim ethers of the general formula I STR1 which have a more specific action and/or a longer-lasting action than PGI2, and to a process for their preparation. The compounds are distinguished by a platelet aggregation-inhibiting action and a blood vessel-relaxing and hypotensive action, and can therefore be used as medicaments.
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- SYNTHESE VON (+/-)-(E)-2-(1-THIA-4-AETOXYCARBONYLBUTYL)-4-(3-HYDROXY-1-OCTENYL)-1Δ-PYRROLIN UND SEINER ANALOGEN
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Starting from 4-methoxycarbonylpyrrolidin-2-one (1) the racemic thiolactim ethers (7a-h) can be obtained via S-alkylation of the thiolactam alcohol (3), subsequent oxidation, Horner-Emmons-Wittig reaction and reduction of the enones.
- Bartmann, W.,Beck, G.,Knolle, J.,Rupp, R. H.
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p. 2947 - 2950
(2007/10/02)
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