Facile Decarboxylation of Nitrobenzeneacetic Acids as a Convenient Route to Alkylnitrobenzenes

A Modular Synthesis of Teraryl‐Based α‐Helix Mimetics, Part 1: Synthesis of Core Fragments with Two Electronically Differentiated Leaving Groups

“…As an example for the second route by vicarious nucleophilic substitution (VNS) towards a diazonium‐based core unit ( 2 b ) we used a protocol developed by Bull and co‐workers for nucleophiles prepared from amino acids 20 . L ‐Valine was converted to the α‐chloroester 9 by using the well‐established diazonium route followed by esterification with SOCl 2 /EtOH (Scheme ) 21.…”

Photochemistry and Thermal Decarboxylation of α‐Phosphoryloxy‐p‐nitrophenylacetates

“…The marked effect of phosphate methylation on the relative sensitivity to decarboxylation of 4 and 5 implies that the charge state of the phosphate is also important. We note that an idiosyncratic thermal decarboxylation of o ‐ and p ‐nitrophenylacetic acid derivatives has also been observed (19) under mildly basic conditions (K 2 CO 3 in warm DMF). Different mechanisms evidently operate for the latter reaction and that reported here, as one is promoted by base while the process we observed occurs in acidic solution.…”

Dibenzo‐fused seven‐membered nitrogen heterocycles by a tandem reduction‐lactamization reaction

“…1 H nmr (DMSO-d 6 ): 9.1-6.0 (br s, 3H), 7.81 (dd, 1H, J = 7.9, 1.6), 7.43 (td, 1H, J = 7.6, 1.6), 7.30 (td, 1H, J = 7.6, 1.1), 7.12 (d, 1H, J = 7.4), 6.90 (td, 1H, J = 7.9, 1.6), 6.63 (m, 2H), 6.44 (td, 1H, J = 7.4, 1.1), 4.12 (s, 2H); 13 C nmr (DMSO-d 6 ): 169. 3, 146.2, 140.7, 131.5, 131.3, 130.6, 130.0, 129.5, 126.7, 126.0, 124.0, 116.0, 114.4, 40.3; ms: m/z 227 (M + ).…”

“…The combined ether layers were washed with water (one time), saturated sodium bicarbonate (three times), sodium chloride (one time), then dried (magnesium sulfate), and concentrated under vacuum. The resulting white solid was triturated with 5% petroleum ether in ether and filtered to give 190 mg (90%) of 11 as a white powder, mp 210-212°; lit mp 210-212° (no solvent given) [19] 167.6, 159.6, 150.9, 134.5, 132.0, 130.6, 125.9, 125.8, 125.2, 125.1, 121.7, 121.3, 120.8 7.70 (dd, 1H, J = 7.6, 0.8), 7.36 (tm, 1H, J = 7.6), 7.06-6.88 (complex, 6H); 13 C nmr (DMSO-d 6 ): 167. 9, 150.4, 139.9, 133.2, 132.1, 129.8, 124.4, 122.9, 122.7, 121.2, 120.7, 119.7, 119.0; ms: m/z 210 (M + ).…”

“…ir: 3175, 1652 cm -1 ; 1 H nmr: 9.25 (br s, 1H), 7.94 (dd, 1H, J = 7.6, 1.1), 7.44 (td, 1H, J = 7.4, 1.4), 7.34-7.25 (complex, 3H), 7.23-7.07 (complex, 3H), 3.95 (s, 2H); 13 C nmr: 170. 1, 141.4, 136.2, 133.0, 132.5, 131.8, 130.8, 128.2, 127.5, 127.1, 127.0, 125.3, 120.9, 39.2; ms: m/z 209 (M + ).…”