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 platforms 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, 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 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 structures 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 jewelry / quantity editor, George R. Newkome -- v. 15. Cumulative topic index
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Additional info for Compr. Heterocyclic Chem. III Vol. 1 Three-membered Heterocycles
The C(2)–N bond of the aziridine 35 36 Aziridines and Azirines: Monocyclic is regiospecifically cleaved by the bromide ion from MgBr2 or the chloride ion from TMSCl via an SN2 process as in 330, and then an intramolecular cyclization by the urea amide nitrogen of 331 gives the corresponding imidazolidinone 332 which corresponds to overall retention of the configuration at C-2 of the orginal aziridine 329 (Scheme 85). 3 Ring expansion with nitriles A direct and efficient route to imidazoline and pyrrolidine derivatives using copper(II) triflate-mediated [3þ2] cycloaddition of various aryl, alkyl, and cycloalkyl N-tosylaziridines with nitriles and olefins as dipolarophiles has been reported <2006TL5399>.
N-Tosyl-protected 2-substituted aziridines 307 underwent regioselective addition of the Pd–TMM complex at the least-hindered site and furnished the functionalized piperidines 308 (TMM ¼ trimethylenemethane). This technique provides an expedient route to enantiopure 2-piperidines because the precursor aziridines are readily prepared in enantiomerically pure from the corresponding amino acids (Scheme 79) <1992SL41>. 2 Grignard addition–cyclization reaction for piperidine synthesis More recently, a stepwise formal [3þ3] cycloaddition sequence via a Grignard addition–cyclization reaction leads to a much improved piperidine synthesis <2005OL2993>.
464) (Scheme 120) <1999TL6503>. There are reports on the use of a Cu(I) complex of ferrocenyldiimine 465 to facilitate nitrene transfer to olefins <1998SL617>. Of particular interest for industrial applications, these reactions can also be efficiently catalyzed by 53 54 Aziridines and Azirines: Monocyclic copper-exchanged zeolite (CuHY) in acetonitrile. , 466). For example, styrene 467 was converted to the corresponding aziridine 468 in 82% yield and 44% ee. The solid-supported catalysts can be easily removed from the reaction mixture, washed, and reused without detrimental effect to catalytic or enantioinductive activity (Scheme 121) <1998CC1601>.
Compr. Heterocyclic Chem. III Vol. 1 Three-membered Heterocycles by Katritzky A.R., et al. (eds.)