Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 28, Pages 4130-4139Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700603
Keywords
Synthetic methods; Heterocycles; Thiol-ynes; Cyclization; Thiazolidin-2-ylideneamine; Anion relay chemistry
Categories
Funding
- Council of Scientific and Industrial Research (CSIR), New Delhi
Ask authors/readers for more resources
Thiol-yne coupling of propargylamine with isothiocyanate has been developed under metal- and solvent-free conditions. The addition of propargylamine to isothiocyanate gives propargylthiourea. This intermediate in situ undergoes intramolecular 5-exo-dig cyclization to give thiazolidin-2-ylideneamine. A through-bond anion relay reaction occurs by attack of the sulfur (not the nitrogen) atom on the alkyne in a highly regioselective manner at ambient temperature. Wide varieties of thiazolidin-2-ylideneamine derivatives were formed in excellent yields.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available