Highly Efficient Regioselective Ring Opening of Aziridines to β-Haloamines in the Presence of β-Cyclodextrin in Water
N. Srilakshmi Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. Rama Rao*
*Organic Chemistry Division-I, Indian Institute of Chemical Technology,
Hyderabad-500 007, India, Email: ramaraokiict.res.in
N. S. Krishnaveni, K. Surendra, M. Narender, Y. V. D. Nageswar, K. R. Rao, Synthesis, 2004, 501-502.
DOI: 10.1055/s-2004-815946
Abstract
Aziridines are opened regioselectively with hydrogen and lithium halides to yield β-haloamines in the presence of β-cyclodextrin using water as the solvent.
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Details
The document discusses a novel and efficient method for the regioselective ring opening of aziridines to form β-haloamines using Ł-cyclodextrin as a catalyst in water. This method addresses the drawbacks of traditional approaches, such as the formation of regioisomer mixtures and the use of expensive, hazardous reagents. Ł-Cyclodextrin, a cyclic oligosaccharide, facilitates the reaction by forming host-guest complexes with aziridines, enhancing selectivity and yield. The process involves dissolving β-cyclodextrin in water, adding aziridine and a hydrogen or lithium halide, and stirring the mixture at room temperature. The reactions yield β-haloamines with high efficiency and minimal side products. Hydrogen halides are preferred over lithium halides for industrial applications due to better yields and shorter reaction times. The method is environmentally friendly, cost-effective, and allows for the recycling of β-cyclodextrin. The products are characterized using IR, NMR, and mass spectrometry. This innovative approach has potential industrial applications and represents a significant advancement in the synthesis of medicinally important compounds.
M. Arjun Reddy, K. Surendra, N. Bhanumathi, K. Rama Rao, Tetrahedron, 2002, 58, 6003-6008.
Key Words
aziridines, hydrogen halides, lithium halides, β-cyclodextrin, water, green chemistry, 1,2-chloroamines, 1,2-bromoamines, 1,2-iodoamines
ID: J66-Y2004-1980