Synthesis of novel 16-spiro steroids: 7-(Aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazolo estrone hybrid heterocycles |
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| Affiliation: | 1. Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia;2. Department of Chemistry, Banasthali Vidyapith, Banasthali, Rajasthan 304022, India;3. Department of Chemistry, University of Jyväskylä, P.O. Box 35, Jyväskylä FI-40014, Finland;4. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt;5. Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box: 2457, Riyadh 11451, Saudi Arabia |
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| Abstract: | The 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the reaction of isatins or acenaphthylene-1,2-dione and 1,3-thiazolane-4-carboxylic acid to various exocyclic dipolarophiles synthesized from estrone afforded a library of novel C-16 spiro oxindole or acenaphthylene-1-one – 7-(aryl)tetrahydro-1H-pyrrolo[1,2-c][1,3]thiazole – estrone hybrid heterocycles. These reactions occur regio- and stereo-selectively affording a single isomer of the spiro estrones in excellent yields with the formation of two C–C and one C–N bonds along with the generation of four new contiguous stereo-centers in a single step. |
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| Keywords: | Estrone 16-Spiro steroids 1,3-Dipolar cycloaddition Azomethine ylide Pyrrolothiazole |
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