Ein Syntheseweg zu Perhydro-3-isochinolinonen mit angulärer Methylgruppe über Organocuprat-Addition

Stanetty, Peter; Bahardoust, M. Hassan; Mihovilovič, Marko D.; Mereiter, Kurt

doi:10.1007/s007060050285

Monatshefte fuer Chemie

1999

DOI: 10.1007/s007060050285

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Ein Syntheseweg zu Perhydro-3-isochinolinonen mit angulärer Methylgruppe über Organocuprat-Addition

Peter Stanetty¹,

M. Hassan Bahardoust²,

Marko D. Mihovilovič³

et al.

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2005

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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

Stanetty¹,

Turner²,

Mihovilovic³

2005

Molecules

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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.

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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

Stanetty¹,

Turner²,

Mihovilovic³

2005

Molecules

View full text Add to dashboard Cite

show abstract

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Ein Syntheseweg zu Perhydro-3-isochinolinonen mit angulärer Methylgruppe über Organocuprat-Addition

Cited by 1 publication

References 0 publications

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

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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