Iodine-promoted Prins-cyclization of ketones – A facile synthesis of spirocyclic-4-iodo-tetrahydropyrans and 5,6-dihydro-2H-pyrans

Yadav, J. S.; Reddy, B. V. Subba; Krishna, V. Hari; Swamy, T.; Kumar, G. G. K. S. Narayana
June 2007
Canadian Journal of Chemistry;Jun2007, Vol. 85 Issue 6, p412
Academic Journal
Homoallylic and homopropargylic alcohols undergo smooth coupling with ketones in the presence of molecular iodine at ambient temperature to produce spirocyclic-4-iodotetrahydropyrans and 5,6-dihydro-2H-pyrans, respectively, in high yields in a short reaction time with high selectivity. The use of molecular iodine makes this procedure quite simple, more convenient, and cost-effective.


Related Articles

  • Diastereoselective reduction of α-aminoketones: Synthesis of anti- and syn-β-aminoalcohols. Fraser, David S.; Park, Sheldon B.; Chong, J. Michael // Canadian Journal of Chemistry;Feb2004, Vol. 82 Issue 2, p87 

    Reduction of N-t-BOC-protected-N-alkyl α-aminoketones with LiEt3BH or Li(s-Bu)3BH furnishes protected syn-β-aminoalcohols with high selectivities. In contrast, removal of the BOC group followed by reduction of the aminoketone gives anti-β-aminoalcohols with variable selectivities. With...

  • Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles. Kayukov, Ya. S.; Kayukova, O. V.; Kalyagina, E. S.; Bardasov, I. N.; Ershov, O. V.; Nasakin, O. E.; Tafeenko, V. A. // Russian Journal of Organic Chemistry;Mar2011, Vol. 47 Issue 3, p392 

    2′-Oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles reacted with oxygencentered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the...

  • Photo-Catalytic Oxidation of Benzyl Alcohols Using Oxone in the Presence of n-Bu4NBr in Water. Shang Wu; Hengchang Ma; Penghua Yan; Jianqiang Wang; Juanjuan Ding; Ziqiang Lei // Letters in Organic Chemistry;Jul2009, Vol. 6 Issue 5, p424 

    A simple, mild and efficient method has been developed for the oxidation of alcohols to aldehydes and ketones using Oxone® as oxidant catalyzed by n-Bu4NBr at room temperature in water under UV lamp for 1 h. Oxone® smoothly oxidizes benzyl alcohol and its derivatives, benzhydrol and its...

  • An Example of Total Synthesis of Flavones by Heck-Sonogashira-Cassar Reaction. Bianco, Armandodoriano; Cavarischia, Claudia; Guiso, Marcella; Matini, Teresa // Letters in Organic Chemistry;Jun2008, Vol. 5 Issue 4, p257 

    The use of aryl vinyl ketones in the Heck reaction for the synthesis of flavonoids was previously described. Herein we present our preliminary study on the reactivity of aroyl alkynes or propargyl alcohols in the Heck-Sonogashira-Cassar coupling reactions to obtain alkynyl precursors of...

  • Efficient oxidation of secondary alcohols to Ketones by NaOCl catalyzed by Salen-Mn(III)/NBS. Zhang, Y.; Lü, F.; Cui, M.; Zhao, J. // Russian Journal of General Chemistry;Oct2014, Vol. 84 Issue 10, p2021 

    An efficient catalytic system salen-Mn(III)/NBS for oxidation of secondary alcohols to ketones by inexpensive and readily available oxidizing agent NaOCl has been developed. The process resulted in good to excellent yields under the action of 2 mol % of salen-Mn(III) and 13 mol % of NBS at room...

  • Highly efficient dehydrogenation of secondary alcohols catalyzed by iridium-CNP complexes. Wang, Dawei; Zhao, Keyan; Yang, Shuyan; Ding, Yuqiang // Russian Journal of General Chemistry;Oct2014, Vol. 84 Issue 10, p2016 

    A new highly practical method is presented for dehydrogenation of secondary alcohols to the corresponding ketones catalyzed by the iridium-CNP complexes. The reactions are compatible with substrates bearing diverse functional groups and proceed efficiently under mild conditions.

  • Reversible covalent chemistry: Alcohols in the mix. Miljani?, Ognjen Š. // Nature Chemistry;Dec2011, Vol. 3 Issue 12, p909 

    The article offers information on the study by researcher Eric V. Anslyn and colleagues concerning the expansion of dynamic combinatorial chemistry (DCC) methodological approach by bulky secondary alcohols' inclusion to robust dynamic assemblies. It says that alcohols may undergo...

  • A mild and efficient method for formation of C-N bond from benzyl alcohols and sulfonamide, carboxamide, 4-nitroanline and azide catalysed by SnCl4. Lingjun Li; Anlian Zhu; Huiwen Yao; Yujing Wei; Di Yang; Jianping Li; Guisheng Zhang // Journal of Chemical Research;Sep2010, Vol. 34 Issue 9, p511 

    A mild and efficient method for the formation of C-N bonds is reported with SnCl4 as an inexpensive catalyst. With 10 mol% of SnCl4, the direct substitution reaction of secondary benzyl alcohols with a sulfonamide, a carboxamide, 4-nitroaniline and an azide proceeds well in good to excellent...

  • A Simple and Highly Selective Biomimetic Oxidation of Alcohols with Hypervalent Iodine(III) Reagent Catalyzed by β-Cyclodextrin in Water. Zhu, Chenjie; Wei, Yunyang // Catalysis Letters;Apr2011, Vol. 141 Issue 4, p582 

    A simple, mild and highly efficient biomimetic oxidation of alcohols to the corresponding aldehydes or ketones with hypervalent iodine(III) reagent catalyzed by β-cyclodextrin was reported. β-cyclodextrin serves as a biological catalyst to enhance the reaction remarkably. The oxidation...


Read the Article


Sorry, but this item is not currently available from your library.

Try another library?
Sign out of this library

Other Topics