By Lorenz T. Biegler;Ignacio E. Grossmann;Arthur W. Westerberg
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Extra info for Systematic Methods of Chemical Process Design (Prentice Hall International Series in the Physical and Chemical Engineering Sciences)
O. Tymoshenko affords furano oxepine 154 in good yield (Equation (22) (2005JOC7679)). Ph Ph O I Cs2CO3, DMA Pd-catalyst O (22) 76% O O 153 154 Ruthenium catalyzed intramolecular propargylation leads to furobenzoxepines 155 in moderate to good yields (Equation (23), 2006EJO881). 1), 4,6-dinitrobenzofuran undergoes condensation with salicylic aldehyde under basic conditions followed by nitro group substitution/cyclization to afford a mono nitro compound with peri-fusion of the benzofuran ring in 68% yield (2005CHE796).
NaNO2 N H H2N S S O O 2. HPF6 83% 278 NH F O 2. N -Me-piperazine R=F 279 S O 1. 2 Benzoxazepines with fused furan ring Benzo[b]benzofuro[2,3-f ][1,4]oxazepine 272 is the sole product obtained from chloro aldehyde 271 and o-aminophenol (Scheme 58 (2001JHC383)). 3 Benzoxazepines with fused thiophene ring Nitro ester 274 undergoes reduction with iron in acetic acid to afford thieno benzoxazepine 275 (Scheme 59 (1994JHC1053)). An alternative route to 275 by the intramolecular formation of a Cthiene–O bond has been reported (2002JHC163).
The corresponding dimethylamino derivative 258 can be constructed in the similar manner. 5 (1996JMC3435, 2002JMC4276)). Similarly, pyrrolo-benzoxazepines 261 are accessible by intramolecular Friedel–Crafts cyclization of acids 260 41 Benzoheteropines with Fused Pyrrole, Furan and Thiophene Rings F Ph 1. DMF/POCl3 N N R HO Ph F O NaH N 2. Grignard 255 N R Ph N 256 257 1. ClCH2CN, ZnCl2; 2. NHMe2 Me F N Me O Ph Me 1. NaBH4 2. NaH O Ph N N Me 1. EtOCOCl 2. NaOH O Ph N HN Me N 259 258 Scheme 54 Et O N Ar O COOH O PCl5 N Et Ar 1.