By Katritzky A.R., et al. (eds.)
Content material: v. 1. 3-membered heterocycles, including all fused platforms containing a 3-membered heterocyclic ring / quantity editor, Albert Padwa -- v. 2. 4-membered heterocycles including all fused platforms containing a 4-membered heterocyclic ring / quantity editor, Christian Stevens -- v. three. 5-membered earrings 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 jewelry 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 jewelry 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 earrings with out bridgehead heteroatom / quantity editor, Ray C.F. Jones -- v. eleven. Bicyclic 5-5 and 5-6 fused ring platforms with not less than one bridgehead (ring junction) N / quantity editor, Janine Cossy -- v. 12. 5- and 6-membered fused platforms 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 earrings and their fused derivatives / quantity editor, George R. Newkome -- v. 14. 8-membered and bigger heterocyclic jewelry and their fused derivatives, different 7-membered earrings / quantity editor, George R. Newkome -- v. 15. Cumulative topic index
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Extra info for Compr. Heterocyclic Chem. III Vol. 5 Five-membered Rings - Triazoles, Oxadiazoles, Thiadiazoles
Sample text
However, a longer reaction time (6 d) is required for 2-methylphenyl azide due to its steric hindrance. 5-Ethoxytriazolines 244, the expected intermediates in this process, readily eliminate ethanol under the reaction conditions and cannot be isolated (Scheme 34) <2002JFC(116)81>. Scheme 34 In reactions with azides, ketones are directly converted to 5-hydroxytriazolines. Ketone enolate 247, generated by treatment of norbornanone 246 with LDA at 0 C, adds readily to azides to provide hydroxytriazolines 248 in 67–93% yield.
Acid chloride 321, obtained in 85% yield by refluxing a solution of carboxylic acid 320 in thionyl chloride, is converted to azide 322 in 86% yield by treatment with sodium azide in pentane. Reactions of azide 322 with amines of low nucleophilicity in refluxing DMF provide ureas 323 in 24–90% yield via Curtius rearrangement. In these reactions, 3-bromo- and 4-bromoaniline give also the corresponding amides, which are formed by simple substitution of the N3 group in azide 322 with amines, as the side products.
Scheme 76 Lithiated N-allylbenzotriazoles 452 and 453 add readily to the CTN bond of Schiff bases derived from aromatic or heteroaromatic aldehydes and amines to give amines 467. In the presence of a palladium catalyst and copper(II) oxidizing agent, amines 467 are smoothly converted to pyrroles 468 (Scheme 77) <2000JOC8074>. Addition of lithiated allylbenzotriazoles 453 to the CTN bond of isothiocyanates leads to thioamides 470. Catalyzed by ZnBr2, thioamides 470 undergo cyclization to aminothiophenes 469 <2001JOC2850>.