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 jewelry with heteroatoms, every one with their fused carbocyclic derivatives / quantity editor, John Joule -- v. five. 5-membered earrings: 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 earrings 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 earrings with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Kenneth Turnbull -- v. 10. Ring platforms with at the very least fused heterocyclic 5- or 6-membered earrings without bridgehead heteroatom / quantity editor, Ray C.F. Jones -- v. eleven. Bicyclic 5-5 and 5-6 fused ring platforms with no less than 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. 9 Six-membered Rings with Three or more Heteroatoms
Any potent nucleophile present may add to the ring and thus initiate ring opening. Steric reasons also play a role; thus, while 5-chloro 4,6-bis(dimethylamino)-1,2,3-triazinium is stable, tris(diisopropylamino)-1,2,3-triazine experiences rearrangement to an imidazolium structure upon reaction with tetrafluoroboric acid <1979CB1535>. Previously, it had been surmised that protonation of ring N-atoms in alkyl- and/or aryl-substituted monocyclic 1,2,3-triazines did not occur due to their presumed low basicity.
33 34 1,2,3-Triazines and their Benzo Derivatives ð5Þ The thermal decomposition of solid 1-methyl-1,4-dihydro-1,2,3-benzotriazin-4-one 59 at >120 C in a stream of argon results in ready loss of N2 with ring contraction to the benzazetinone 60 (Equation 6), which was identified by matrix isolation at 15 K (IR: CTO at 1843 cmÀ1). Irradiation of 60 results in photoreversible ring opening to the iminoketene 61, characterized by an IR band at 2125 cmÀ1 and a UV absorption centered at 420 nm <1989CC1777>.
Dehydrogenation of their alcohol function with manganese dioxide affords formal Friedel–Crafts acylation products <1998MI119>. 5. 4 Reactions with Nucleophiles Nucleophiles relevant for this chapter are hydride ion, O-atom- and N-atom-centered nucleophiles and C-nucleophiles like organometallic compounds, ketene acetals, and ester enolates as well as electron-rich heterocycles. Reductions of 1,2,3-triazines and 2-methyl-1,2,3-triazin-2-ium salts by sodium borohydride in methanol and lithium alanate in ether to yield 2,5-dihydro-1,2,3-triazines have been reviewed in CHEC(1984) and CHEC-II(1996).
Compr. Heterocyclic Chem. III Vol. 9 Six-membered Rings with Three or more Heteroatoms by Katritzky A.R., et al. (eds.)