Intramolecular Cascade Lactone Cyclization of Dicoumarol Derivatives Promoted by Tributyltin Chloride

Author(s): Sadia Rehman, Muhammad Ikram, Fazle Subhan.

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 3 , 2014

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Abstract:

Dicoumarols, derived from aldehydes with ortho hydroxy substitution (5 and 7), were successfully cyclized by Sn(n-Bu)3Cl in THF as a reaction medium. Catalytic cycle reveals the formation of HO-Sn-O=C cyclic intermediate which is rearranged and isomerized to the cyclic lactone. N-butane was released by Sn(n-Bu)3Cl leaving behind Sn(n- Bu)2(OH)Cl keeping the catalytic route continued unless the two butane attached to tin were also consumed. The products produced were characterized using 1H, 13C{1H}-NMR, high resolution EI-MS, IR and elemental analyses. Single crystals of 6 were grown in P1 space group from concentration in THF and structurally studied using X-ray diffraction analysis. All the spectroscopic and analytical studies supported the formation of the cyclized products.

Keywords: Sn(n-Bu)3Cl, dicoumarol, intramolecular cyclization, single crystal study, lactone.

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Article Details

VOLUME: 11
ISSUE: 3
Year: 2014
Page: [215 - 219]
Pages: 5
DOI: 10.2174/1570178610666131210233841
Price: $65

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