Heterocyclic Chemistry by J. A. Joule, K. Mills, G. F. Smith

By J. A. Joule, K. Mills, G. F. Smith

Three. four Electrocyclic methods in heterocyclic ring synthesis sixty one three. five Nitrenes in heterocyclic ring synthesis sixty two References for bankruptcy three sixty three four commonplace reactivity of pyridines, quinolines and isoquinolines sixty four five Pyridines: reactions and synthesis seventy two five. 1 Reactions with electrophilic reagents seventy three five. 2 Reactions with oxidising brokers seventy nine five. three Reactions with nucleophilic reagents eighty five. four Reactions with bases eighty two five. five Reactions of C-metallated pyridines eighty three five. 6 Reactions with radical reagents eighty five five. 7 Reactions with decreasing brokers 86 five. eight Electrocyclic reactions (ground nation) 87 five. nine Photochemical reactions 88 five. 10 Oxy-and aminopyridines 89 five. eleven Alkylpyridines ninety four five. 12 Pyridine aldehydes, ketones, carboxylic acids and esters ninety five five. thirteen Quatemary pyridinium salts ninety five five. 14 Pyridine N -oxides 10 1 five. 15 Synthesis of pyridines 104 References for bankruptcy five 111 workouts for bankruptcy five 118 6 Quinolines and isoquinolines: reactions and synthesis a hundred and twenty 6. 1 Reactions with electrophilic reagents 121 6. 2 Reactions with oxidising brokers 123 6. three Reactions with nucleophilic reagents 123 6. four Reactions with bases a hundred twenty five 6. five Reactions of C-metallated quinolines and isoquinolines 126 6. 6 Reactions with radical reagents 126 6. 7 Reactions with decreasing brokers 126 6. eight Electrocyclic reactions (ground nation) 127 6. nine Photochemical reactions 128 6. 10 Oxyquinolines and -isoquinolines 128 6. eleven Aminoquinolines and -isoquinolines one hundred thirty 6. 12 Alkylquinolines and -isoquinolines a hundred thirty 6.

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Academic Press, New York, 1960-72. , Wiley-Interscience, 1976. 3 'Aromaticity of heterocycies', Cook, M. , Katritzky, A. , Adv. Heterocycl. , 1974, 17, 257; 'Aromaticity of heterocycies: experimental realisation of Dewar-Breslow definition of aromaticity', Hosmane, R. A. and Liebman, J. , 1991,32,3949; 'The relationship between bond type, bond order and bond lengths. Are-evaluation of the aromaticity of some heterocyciic molecules', Box, V. G. , Heteroeycles, 1991, 32, 127; 'The coneept of aromaticity in heteroeyciie ehemistry', Simkin, B.

For example, simple pyridines do not undergo many useful electrophilic substitutions, but quinolines and isoquinolines undergo substitution in the benzene ring. It has been estimated that the intrinsic reactivity of a pyridine (Le. not protonated) to electrophilic substitution is around 107 times less than that of benzene, that is to say, about the same as that of nitrobenzene. When quinoline or isoquinoline undergo nitration in the benzene ring the ----lil '--_ _ _E_L_E_C_TR_O_PH_I_L_IC_S_U_B_S_T_IT_UT_IO_N_A_T_C_A_R_B_O_N_ _ _ actual species attacked is the N-protonated heterocycle, and even though substitution is taking place in the benzene ring, it must necessarily proceed through a doubly charged intermediate: this results in a much slower rate of substitution than for the obvious comparison, naphthalene - the 5- and 8-positions of quinolinium are attacked at about a 10 10 slower rate than the I-position of naphthalene, and it was estimated that the nitration of pyridinium cation is at least 105 slower stillJ A study of the bromination of methylpyridines in acidic solution allowed an estimate of 10- 13 for the partial rate factor for bromination of a pyridinium cation.

O o [D I N/. 1 Direct lithiation (C-hydrogen-deprotonation) Many heterocyclic systems react directly with alkyllithiums or with lithium amides to give the lithio-heterocycle via abstraction of a proton. 58 Lithiations by deprotonation are therefore directly related to base-catalysed proton exchange59 using reagents such as sodium methoxide, at O_R_G_A_N_O_M_E_T_A_L_L_IC_D_E_R_I_V_A_TI_V_E_S__________~II L -_ _ _ _ _ _ _ _ _ _ much higher temperatures, which historically provided the first indication that preparative deprotonations might be regioselective and thus of synthetic value.

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