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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 ordinary 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 country) 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 one hundred 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 country) 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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Nm) 1t-1t* 1t-+1t Amax. (nm) E E 270 450 195 7500 340 298 328 271 315 326 1040 410 2000 2750 5300 1400 2030 5600 3210 5500 8500 200 - 251 257 256 246 243 260 243 242 269 254 220 204 1400 7400 The bicyclic azines have much more complex electronic absorption, and the n - n* and n - n* bands overlap; being much more intense, the latter mask the former. 2). 2 Ultraviolet spectra of bicycIic azines (fine structure not given) HeterocycIe Am... (nm) Am... (nm) Amax. (nm) E E E Quinoline Quinolinium Isoquinoline Isoquinolinium Quinolizinium Naphthalene 313 313 317 331 324 312 270 226 233 217 228 225 220 2360 6350 3100 4170 14500 250 3880 35500 34700 37000 37500 17000 100000 266 274 284 275 4030 1960 2700 5600 11 12 IIL_____________A_R_O_M_A_TI_e_H_E_TE__R_O_e_Y_e_L_ES____________~ The UV spectra of the simple five-membered heteroaromatic systems all show just one medium-to-strong low-wavelength band with no fine structure.

They have usually been prepared by exchange reactions 116 (in situ) of zinc halides with heteroaryllithiums but this method limits their usefulness. Efficient methods are now available for their direct preparation from zinc metal and the heteroaryl halide in both electron-rich and electron-poor systems. 4 Side-chain metallation of 6-membered heterocycles ('lateral metallation ') Anions on alkyl side-chains and immediately adjacent to a heterocyclic ring are subject to varying degrees of stabilisation by interaction with the ring.

73 Lithiation at the other hetero-ring position can be achieved via halogen exchange, but low temperatures must be maintained to prevent equilibration to the more stable 2-lithiated heterocycle. 65 ~__________O_R_G_AN __O_ME ___ TA_L_L_I_C_D_E_R_IV_A_TI __V_E_S__________~II Qjr ~ ~ N l t-BULi/-l00oC. 14 The 1,3-azoles lithiate very readily, at C-2. 4) with that at the

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