By Moody C.J.
This quantity incorporates a diversity of themes resembling the activation and manipulation of pyrroles, the synthesis of annelated pyrroles utilizing acylation reactions and the synthesis of kainoids, a family members of hugely biologically lively nitrogen heterocycles.
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Additional resources for Advances in Nitrogen Heterocycles, Volume 3
B) Hodges, L. ; Spera, M. U; Moody, M. ; Harman, W. D. J. Am. Chem. Soc. 1996, 118, 7117. 14. ; Koontz, J. ; Hodges, L. ; Nilsson, K. ; Neely, L. ; Myers, W. ; Harman, W. D. J. Am. Chem. Soc. 1995, 117, 3405. 15. The pentaammineosmium(II) metal center also binds in a dihapto fashion to several other classes of aromatic molecules, including benzenes, naphthalenes, phenols, anisoles, anilines, furans, and thiophenes, activating them toward further functionalization. The reactivity and synthetic utility of these complexes are the subject of a recent review: Harman, W.
CDMAc used as solvent. dTrapped in situ. eReaction carried out at -50 ~ in 2:1 MeCN/EtCN. Synthesis of Indoles The conversion of tetrahydroindole complexes to indoles is achieved in moderate to good yields by heating in the presence of 2 equiv of DDQ in either acetonitrile or DMAc solution, the latter of which gives slightly higher yields (Table 11). In this reaction, the oxidant serves both to Ph, if) 0 Me ~ MeO2G_. Os Me 122 Me Me02C ~ 1 Me 5 0 Os 39 Osmium Activation of Pyrroles Table 11. Synthesisof Indoles from rl2-Pyrrole Complexes I RI Precursor 122 149 150 151 152 153 155 156 157 158 159 160 161 163 164 178 28 28 Notes: Me Me Me Me Me Me Me Me Me Me Me Me R4 Me Ph Me Ph Ph H OMe OMe H H CO2Me Ph H H Me Me Me Me Me Et 9 Rs R5 H H H H H H H H Ac CO2Me CO2Me Ac Ac Me -(CH2)4-(CH--CH)EPh H Me H R6 R4 R7 -C(O)N(Ph)C(O)-C(O)N(Ph)C(O)CO2Me CO2Me CO2Me CO2Me H CO2Me -C(O)N(Ph)C(O)-C(O)N(Ph)C(O)H CO2Me -C(O)N(Ph)C(O)-C(O)N(Ph)C(O)-C(O)N(Ph)C(O)-C(O)N(Ph)C(O)-C(O)N(Ph)C(O)-C(O)CHEC(O)-C(O)N(Ph)C(O) -C(O)N(Ph)C(O) -C(O)N(Ph)C(O) COEMe COEMe Indole 123 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179b 165c 166c Yielda 58 (74) 48 (60) 35 (42) 48 (55) 39 (49) 7 (12) 29 (37) 12 (17) 46 (52) 14 (17) 49 (66) 22 (27) 4(5) 9 (14) 38 (45) 16 (40) 37 40 aYields listed are from the uncomplexed pyrrole; numbers in parentheses represent yields from the precursor.
19. In the Diels-Alder reactions of cyclopentadiene, an endo transition slate leads to an endo-subsfituted product. In the dipolar cycloadditions reported here, an endo transition state leads to an exo-substituted product. 20. The donor number (DN) is defined as the negative AH value for the solvation of SbC15 by a donating solvent in 1,2-dichloroethane solution: Gutman, V. The Donor-Acceptor Approach to Molecular Interactions, Plenum Press: New York, 1978, Chapter 2. 21. ; Grandclaudon, P. J. Chem.