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Synthesis of 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones and reaction thereof with acetic anhydride |
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| Authors: | Vasiliy V Shchepin Pavel S Silaychev |
| Institution: | a Organic Chemistry Division, Chemistry Department, Perm State University, ul. Bukireva 15, Perm 614990, Russia b PermNIPIneft Ltd, ul. Sovetskoy Armii 29, Perm 614066, Russia c I. Ya. Postovskiy Institute of Organic Synthesis, Russian Academy of Sciences, Ural branch, ul. S. Kovalevskoy 20, Yekaterinburg 620219, Russia |
| Abstract: | The reaction of zinc enolates synthesized from 1-aryl-2,2-dibromoalkanones and zinc with 6-R-2-oxochromene-3-carboxylic acid N-benzylamide affords 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta2,3]cyclopropa1,2-a]naphthalene-3,4-diones. Acylation of these compounds is accompanied by an unexpected rearrangement producing a sole geometrical isomer of 4′-alkyl-5′-aryl-1′-benzyl-3,4,2′,3′-tetrahydro-2,2′-dioxospirochroman-3,3′-pyrrol]-4-yl acetates. |
| Keywords: | 1-Aryl-2 2-dibromoalkanones Zinc Zinc enolate 2-Oxochromen-3-carboxylic acid N-benzylamide 1 2 9b 9c-Tetrahydro-5-oxo-2-aza-cyclopenta[2 3]cyclopropa[1 2-a]naphthalene-3 4-diones 3 4 2&prime 3&prime -Tetrahydro-2 2&prime -dioxospiro[chroman-3 3&prime -pyrrole]-4-yl acetates |
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