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 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 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 earrings with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Kenneth Turnbull -- v. 10. Ring structures with not less than fused heterocyclic 5- or 6-membered jewelry without bridgehead heteroatom / quantity editor, Ray C.F. Jones -- v. eleven. Bicyclic 5-5 and 5-6 fused ring platforms with a minimum of 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 earrings and their fused derivatives, different 7-membered jewelry / quantity editor, George R. Newkome -- v. 15. Cumulative topic index
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Extra resources for Compr. Heterocyclic Chem. III Vol. 8 Six-membered Rings with Two Heteroatoms
Initially, when halopyridazin3(2H)-ones were used the acidic NH was always blocked with a substituent. As NH protecting group a MOM group has been most frequently used <1999S1666, 2001TL8633>. More recently, a hydroxymethyl group has been introduced <2003TL4459>. This seems to be the preferred protecting group since it can easily be introduced via Pyridazines and their Benzo Derivatives reaction of the pyridazin-3(2H)-one substrate with formaldehyde. After the Pd-catalyzed reaction, it is in situ removed via a base induced or thermal retro-ene reaction <2004COR1463> which avoids an additional deprotection step.
Triflate esters also allowed chemoselective Pd-catalyzed reactions versus a chlorine atom. Sonogashira reaction on Pyridazines and their Benzo Derivatives Scheme 41 4-chloro-2-methyl-5-trifluoromethanesulfonyloxypyridazin-3(2H)-one 157 and 5-chloro-2-methyl-4-trifluoromethanesulfonyloxypyridazin-3(2H)-one 155 yielded respectively smooth C-5 and C-4 selective alkynylation <2001T10009>. 1. Triflate esters in the benzene ring of a phthalazin-1(2H)-one have also been used in Sonogashira reactions. Interestingly, there seems to be no need for N–H protection in this case <2000BML2235>.
The respective hydrazones could be cyclized with Br2 in MeOH or Pb(OAc)4 to s-triazolo[4,3-b]pyridazin-3-yl substituted polyols <1997JHC1115, 1998JHC513>. 1]octan-3-one was reacted with pyridazine-3-hydrazines and the resulting mixtures were subsequently treated with Pb(OAc)4. Besides s-triazolo[4,3-b]pyridazine formation also diazenes were obtained. This can be rationalized by the enehydrazine–hydrazone mixtures observed in the first reaction. For phthalazin-1-hydrazines only diazenes were obtained after oxidation <2005TA2927>.