Asian Journal of Research in Chemistry

Open Access Open Access  Restricted Access Subscription Access
Open Access Open Access Open Access  Restricted Access Restricted Access Subscription Access

Microwave-Assisted Efficient and Chemoselective Reduction of aldehydes with Thiourea dioxide


Affiliations
1 Department of Chemistry, Punjab Agricultural University, Ludhiana-141004, Punjab, India
     

   Subscribe/Renew Journal


An efficient, inexpensive and chemoselective method using microwave assisted irradiation with thiourea dioxide for the reduction of aldehydes to the corresponding alcohols has been developed. Under the reaction conditions, reduction of the ketones does not occur and the alcohols from the corresponding aldehydes are obtained, in shorter time over the reported one, in excellent yields.

Keywords

Reduction, Thiourea Dioxide, Aldehydes, Microwave Irradiations
Subscription Login to verify subscription
User
Notifications
Font Size


  • Zeynizadeh B and Setamdideh D. A new synthetic method for mild and convenient reduction of nitroarenes. Synthetic Communication 36; 2006: 2699-2701.

  • Zeynizadeh B and Behyar T. Fast and efficient method for reduction of carbonyl compounds with NaBH4/wet SiO2 under solvent free condition. Journal of Brazilian Chemical Society 16; 2005: 1200-1209.

  • Halimjani AZ and Saidi M R. Sodium borohydride-solid LiClO4: An effective reagent for reducing aldehydes and ketones in aprotic solvent. Synthetic Communication 35; 2005: 2271- 2276.

  • Zeynizadeh B andYahyaei S. A mild and convenient method for the reduction of carbonyl compounds with NaBH4 in the presence of catalytic amount of MoCl5. Bulletin of Korean Chemical Society. 24; 2003: 1664-1670.

  • Dhillon R S, Nayyar K and Singh J. Hydroboration of functionalized olefins with acetoxyborohydride. Tetrahedron Letters 33; 1992: 6015-6016.

  • Tanemura K, Suzuki T, Nishida Y, Satsumbayashi K and Horaguchi T. Chemoselective reduction of aldehydes in the presence of ketones with NaBH4 in polyethylene glycol dimethyl ethers. Synthetic Communication 35; 2005: 867-872.

  • Singh J, Kad GL, Sharma M and Dhillon R S. Chemoselective carbonyl reduction of functionalized aldehydes and ketones to alcohols with sodium dithionate. Synthetic Communication 28; 1998: 2253-2257.

  • Chandrasekhar S, Reddy R and Ramarao C. Chemoselective reduction of carbonyl compounds with PMHS-ZnCl2. Synthetic Communication 27; 1997: 2251-2254.

  • Dhillon R S, Singh R P and Kaur D. Selective 1,4-reduction of conjugated aldehydes and ketones in the presence of unconjugated aldehydes and ketones with sodium dithionate. Tetrahedron Letters. 36; 1995: 1107–1108.

  • Gautam VK, Singh J and Dhillon RS. Selective hydroboration studies with acetoxyborohydride. Journal of Organic Chemistry. 53; 1988: 187-189.

  • Sambher S, Baskar C and Dhillon RS. Novel chemoselective reduction of aldehydes in the presence of other carbonyl moieties with thioureadioxide. Synthetic Communication 38; 2008: 2150–2157.

  • White L L and Kittredge KW. A microwave-assisted reduction of cyclohexanone using solid-state-supported sodium borohydride. Journal of Chemical Education. 82; 2005: 1055-1056.

  • Varma SV and Saini RK. Microwave assisted reduction of carbonyl compounds in solid state using sodium borohydride supported on alumina. Tetrahedron. 38; 1997: 4337-4339.

  • Shankaraiah N, Markandeya N, Moraga ME, Arancibia C, Kamal A and Santos LS. Synthesis 13; 2009: 2163-2170.

  • Daneault C and Leduc C. Cellular Chemical Technology. 28; 1994: 205–217.

  • Gacen J and Cegarra J. Journal of Society of Dyers Colourist. 107: 138–141 (1991).

  • Shashova VE. Formamidine sulfinic acid as a biochemical reducing agent. Biochemistry 3; 1964: 1719-1720.

  • Robertson J. G. Determination of subunit dissocation constants in native and inactivated CTP synthetase by sedimentation equilibrium. Biochemistry 34; 1995: 7533-7541.

  • Borgogno G, Colonna S and Fornasier R. Reduction of organicsulfur compounds by formamidinesulfinic acid under phase-transfer conditions. Synthesis 1975: 529-530.

  • Drabowicz J, Mikolajczyk M. An iodine-catalysed reduction of sulfoxides by formamidinesulphinic acid. Synthesis 1978: 542

  • Vlasova EA, Makarov SV and Malinkina MN Russian Journal of Physical Chemistry A. 84; 2010: 573-577.

  • Lang E. S and Comasseto J. V., Synthetic Communication. 18: 301-305 (1988).

  • Te´rcio T., Ferreira B., De Oliveira A. R. M. and Comasseto J. V., Synthetic Communication. 19, 239-244 (1989).

  • Gore P. H. Chem. Ind. (London) 1355 (1954).

  • dos Santos RB, Brocksom TJ and Brocksom U. A convenient deoxygenation of ,-epoxy ketones to enones. Tetrahedron Letters. 38; 1997: 745-748.

  • Balicki R and Chmielowiec U. A mild deoxygenation of heterpoaromatic Noxides by formamidinedinesulfinic acid. Monatsh Chemistry. 131; 2000: 1105-1107.

  • Gao Q, Liu B, li L and Wang J. Oxidation and Decomposition Kinetics of Thiourea Oxides. Journal of Physical Chemistry A. 111(5); 2007: 872-877.

  • Makarov SV. Recent trends in the chemistry of sulfur-containing reducing agents. Russian Chemical Reviews. 70; 2001: 885-895.


Abstract Views: 372

PDF Views: 2




  • Microwave-Assisted Efficient and Chemoselective Reduction of aldehydes with Thiourea dioxide

Abstract Views: 372  |  PDF Views: 2

Authors

Urvashi
Department of Chemistry, Punjab Agricultural University, Ludhiana-141004, Punjab, India
Ranjit Singh Dhillon
Department of Chemistry, Punjab Agricultural University, Ludhiana-141004, Punjab, India

Abstract


An efficient, inexpensive and chemoselective method using microwave assisted irradiation with thiourea dioxide for the reduction of aldehydes to the corresponding alcohols has been developed. Under the reaction conditions, reduction of the ketones does not occur and the alcohols from the corresponding aldehydes are obtained, in shorter time over the reported one, in excellent yields.

Keywords


Reduction, Thiourea Dioxide, Aldehydes, Microwave Irradiations

References