Compr. Heterocyclic Chem. III Vol. 5 Five-membered Rings - by Katritzky A.R., et al. (eds.)

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 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, each 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 earrings 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 earrings with out bridgehead heteroatom / quantity editor, Ray C.F. Jones -- v. eleven. Bicyclic 5-5 and 5-6 fused ring platforms with at the least 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 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. 5 Five-membered Rings - Triazoles, Oxadiazoles, Thiadiazoles

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Nevertheless, 1-(g-phenylallyl)benzotriazole 484 is still lithiated exclusively at the carbon as it is evident from its reaction with aldehydes and ketones leading to dienes 486, resulting from 59 60 1,2,3-Triazoles elimination of benzotriazole and water from intermediate carbinols 485 <1997JOC238>. However, the strongly electron-withdrawing phenylsulfonyl group at the g-carbon shifts the equilibrium from form 487 to form 488, which upon its alkylation gives sole product 489 (Scheme 79) <1998JHC173>.

Treated with trifluoroacetic anhydride, sulfoxides 218 undergo conversion to triazapentalenes 219 with high yields. The process must involve acylation of the sulfoxide oxygen atom and generation of a carbocation that attacks the N-2 atom of benzotriazole. Hydrogenation over Raney nickel cleaves the C–S and one of the N–N bonds to generate ortho-substituted anilines 220 (Scheme 27) <2002EJO493>. Scheme 27 Addition of benzotriazole to 1-phenyl-2-aroylacetylenes gives , -unsaturated ketones 221 in high yields.

When the reaction mixture is kept for an extended period of time at À78  C, (Z)- 391 and (E)- 392 alkenes are formed. When benzophenone is added to the reaction mixture, alcohols 387 are obtained in good yields; however, benzaldehyde does not react under these conditions (Scheme 63). Scheme 63 1,2,3-Triazoles In a direct comparison of the reactivity of 1-alkyl- and 2-alkylbenzotriazoles, compound 393 was lithiated in the presence of benzophenone with 1 equiv of LDA to give a mixture of alcohol 394 and dimer 395 (Equation 12) <1996LA745>.

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