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One-pot synthesis of new spiro[cyclopropane-1,3′-[3H]indol]-2′(1′H)-ones from 3-phenacylideneoxindoles

✍ Scribed by Masoud Shaabanzadeh; Faranak Khabari

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
410 KB
Volume
47
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

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In a one‐pot procedure, the 3‐phenacylideneoxindoles 1a, 1b, 1c, 1d were reacted with hydrazine and then in situ with lead(IV) acetate and new diastereoisomers of spiro[cyclopropane‐1,3′‐[3__H__]indol]‐2′(1′H)‐ones were prepared. Compounds 1a, 1b, 1c, 1d underwent a highly diastereoselective cyclopropanation leading to diastereoisomers 2a, 2b, 2c, 2d. These new compounds containing both 2‐oxindole and cyclopropane moieties may be valuable in medicinal chemistry. J. Heterocyclic Chem., (2010).

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