Research Article

Flow and Microwave Induced Pellizzari Reactions: Synthesis of Heterocyclic Analogues of the Benzoxazepine Antipsychotic Agents Loxapine and JL-13

Table 1

Intramolecular cyclization to form triazolo benzoxepines 3 (% isolated yield).

Entry3Ar

13aPh385457
23b2-Cl-C6H4488678
33c4-Cl-C6H4669684
43d2-OH-C6H42989>99
53e4-OH-C6H4416772
63f3-OMe-C6H4289282
73g3-pyridyl578498
83h2-F-C6H42588>99
93i3-F-C6H4328385
103j4-Me-C6H4399888
113k3-NO2-C6H4178185
123l3-Cl-C6H44480

-BuOH, , 118°C, 6 h;  W, 200°C, -BuOH 15 min. pumps of the reactor were set to flow at equal rates (2 μl/min) at 190°C with a solution of 5-chlorobenzo[b]pyrido[,-f][,]oxazepine (0.04 M) and hydrazide (0.04 M) in -BuOH with residence time of 2.5 min. Experiments represent .