Chemistry

Compr. Heterocyclic Chem. III Vol.12 Five- and Six-membered by Katritzky A.R., et al. (eds.)

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, 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 jewelry with 3 or extra heteroatoms, and their fused carbocyclic derivatives / quantity editor, Kenneth Turnbull -- v. 10. Ring structures with no less than 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 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 jewelry and their fused derivatives, different 7-membered earrings / quantity editor, George R. Newkome -- v. 15. Cumulative topic index

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3 Formation of ,
-bonds An intramolecular formal aza-[3þ3] cycloaddition reaction based on the cyclization of a vinylogous amide tethered with an , -unsaturated iminium moiety was applied to the synthesis of the indoloquinolizidine alkaloids tangutorine <2003OL4709> and deplancheine 14 <2005OBC2140>. The key step of the latter synthesis (Scheme 80) involved the double enamine cyclization of precursor 354 to 356 in the presence of piperidinium acetate, through the intermediacy of 355, followed by catalytic hydrogenation.

From that date, this strategy has become more and more common in quinolizidine synthesis, especially in cases where the cyclization takes place by formation of a bond to the heteroatom. Some examples are given below. In a formal synthesis of quinolizidine 233A 296, the 2,6-cis-disubstituted piperidine 292, as a mixture of diastereomers, was transformed into 293 by N-acylation with but-3-enoyl chloride. An RCM afforded 294, which was transformed into 295 by hydrogenation of the double bonds and hydride reduction of the lactam, thereby completing a formal synthesis <2000JOC8908> of quinolizidine 233A 296 (Scheme 65) <2004JA4100>.

Treatment of this compound with nucleophiles afforded mixtures of indolizine and quinolizine derivatives in Bicyclic 6-6 Systems with One Bridgehead (Ring Junction) Nitrogen Atom: No Extra Heteroatom O NH N H + Cl 75% S H S 391 i, Ra-Ni ii, LiAlH4 N N N H H 90% Br N N H H CH2 4 O S H O N N H Br 390 N H H CH2 4 i, heat ii, Et3N, heat O S H H2C 394 393 392 Scheme 90 varying amounts, that depended on the nature of the nucleophile. 5:1 mixture of compounds 399 and 400 (Scheme 91). Assistance to the nucleophilic attack by the indolizine nitrogen was proved by the detection of intermediate 398 by 1H NMR spectroscopy; quinolizine formation requires attack of the nucleophile to the more substituted carbon atom of the aziridinium ring, which was explained by the development of a partial positive charge in the transition state, which is more stabilized at the most substituted carbon atom <2003JOC9598>.

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