By Katritzky A.R., et al. (eds.)
Content material: v. 1. 3-membered heterocycles, including all fused structures containing a 3-membered heterocyclic ring / quantity editor, Albert Padwa -- v. 2. 4-membered heterocycles including all fused structures containing a 4-membered heterocyclic ring / quantity editor, Christian Stevens -- v. three. 5-membered jewelry with one heteroatom including their benzo and different carbocyclic-fused derivatives / quantity editors, Gurnos Jones, Christopher A. Ramsden -- v. four. 5-membered earrings with heteroatoms, every one with their fused carbocyclic derivatives / quantity editor, John Joule -- v. five. 5-membered jewelry: triazoles, oxadiazoles, thiadiazoles and their fused carbocyclic derivatives / quantity editor, Viktor V. Zhdankin -- v. 6. different 5-membered earrings with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Viktor V. Zhdankin -- v. 7. 6-membered jewelry with one heteroatom, and their fused carbocyclic derivatives / quantity editor, David StC. Black -- v. eight. 6-membered earrings with heteroatoms, and their fused carbocyclic derivatives / quantity editor, R. Alan Aitken -- v. nine. 6-membered jewelry with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Kenneth Turnbull -- v. 10. Ring structures with at the very least fused heterocyclic 5- or 6-membered jewelry with out bridgehead heteroatom / quantity editor, Ray C.F. Jones -- v. eleven. Bicyclic 5-5 and 5-6 fused ring structures with a minimum of one bridgehead (ring junction) N / quantity editor, Janine Cossy -- v. 12. 5- and 6-membered fused structures with bridgehead (ring junction) heteroatoms concluded: 6-6 bicyclic with one or N or different heteroatoms; polycyclic; spirocyclic / quantity editor, Keith Jones -- v. thirteen. 7-membered heterocyclic jewelry and their fused derivatives / quantity editor, George R. Newkome -- v. 14. 8-membered and bigger heterocyclic earrings and their fused derivatives, different 7-membered earrings / quantity editor, George R. Newkome -- v. 15. Cumulative topic index
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Additional info for Compr. Heterocyclic Chem. III Vol. 2 Four-membered Heterocycles
An olefinic group at C-3 in azetidin-2-ones has been transformed into a formyl group by ozonolysis, and into a dimethoxymethyl group by ozonolysis and subsequent treatment with trimethoxymethane <2001J(P1)2566>. ð126Þ ð127Þ ð128Þ Azetidines, Azetines and Azetes: Monocyclic ð129Þ Isomerization of cis-azetidin-2-ones to trans-azetidin-2-ones has been observed either thermally (Equation 130) <2000JOC4453> or in the presence of a base as a catalyst (Equation 131) <2000JOC3459>. A formyl group in azetidin-2-ones undergoes Wittig-olefination <2000JOC3459>.
Removal of t-butyldimethylsilyl (TBDMS) is reported on treatment with TBAF (Equation 146) <1996TL6495>. Magnesium monoperoxyphthalate in methanol successfully cleaved the N–N bond of N-(1-pyrrolidinyl)azetidin-2-one 372 (Equation 147) <2000AGE2893> and of N-(N9-methyl-N9-p-tolyl)aminoazetidin-2-ones <2003T10195> to give the corresponding 1-unsubstituted azetidin-2-ones. ð141Þ ð142Þ 57 58 Azetidines, Azetines and Azetes: Monocyclic ð143Þ ð144Þ ð145Þ Scheme 54 ð146Þ ð147Þ Reductive O-debenzylation yielded N-hydroxyazetidin-2-one 373 (Scheme 55) <2000T5719>.
3 Experimental Structural Methods The infrared (IR) spectra of azetidin-2-ones show a strong absorption around 1745 cmÀ1. However, the carbonyl group in N-benzyl- or benzhydryl-substituted azetidin-2-ones absorb at around 1770–1780 cmÀ1 <2003S2483>. The most powerful tool for the determination of relative stereochemistry of azetidin-2-ones is 1H NMR spectroscopy. 5 Hz for transderivatives. The 13C NMR spectra of azetidin-2-ones show the typical carbonyl resonance at 166–170. However, values outside this range are possible if strong electron-withdrawing or electron-donating groups are present on the adjacent carbon atoms.