By Alan R. Katritzky
The definitive serial within the box — because 1960.* presents up to date fabric on a quick starting to be and hugely topical topic sector* comprises the most recent examine overlaying a large choice of heterocyclic subject matters* Written via top experts and designed as a guide for college students and and educational researchers
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Extra info for Advances in Heterocyclic Chemistry, Vol. 96
2 Pyrrolo-benzoxazepines with other fusion modes. 4 (2006T6018)). 1-[2-Aryloxyethyl]-5-benzotriazolyl-2-pyrrolidinones 269 (X ¼ O) and the corresponding isoindolinones (not depicted) undergo Lewis acid mediated cyclizations to 1,4-benzoxazepines 270 (X ¼ O) (Equation (33) (2001JOC5590)). X O X N Bt TiCl4 N O 269 270 (33) 43 Benzoheteropines with Fused Pyrrole, Furan and Thiophene Rings OH O O N 1. EtOH 2. DMF Cl H2, Pd/C; AcOH, Ac2O O NH2 CHO NH O OAc 271 272 273 Scheme 58 COOCH3 COOCH3 COOCH3 S H3COOC Lawesson s reagent S Fe, AcOH O O O NH R S O NO2 R 274 S N H R 275 276 N -Me-piperazine R = COOMe R1 O 1.
Triphosgene H N 2. 2 Pyrrolo-benzothiadiazepines Syntheses of this class of compounds usually involve 1,2,5-thiadiazepine ring 333 (Figure 6) which is stable in the S-oxidized form and structurally represents cyclic pyrrole N-sulfonyl derivatives. Most of the synthetic strategies include formation of an S–Npyrrole bond in the early stages. A final cyclization step typically includes (i) intramolecular cyclization by creation of an N–X bond from a suitable pyrrole precursor or (ii) a 6 + 1 type cyclization that involves dielectrophilic species to form linker X and utilizes the nucleophilicity of the phenyl amino group and of the pyrrole ring at C2.
Reductive ring closure of 1-(2-nitrobenzyl)-2-pyrrole carbaldehyde 200 results in pyrrolo[2,1-c][1,4]benzodiazepine 201 (Scheme 42 (1999BMCL1737)). On the other hand, oxo derivative 203 can be synthesized starting from aldehyde 200 through a nitrile formation/cyclizations multistep sequence. The alternate synthetic strategy included reduction of the intermediate acid (R ¼ H) or ester (R ¼ Et) 205 followed by CDI or thermal cyclization (1992JHC1005). 33 Benzoheteropines with Fused Pyrrole, Furan and Thiophene Rings 1.
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