✍ Scribed by Richard A. Bunce; James E. Schammerhorn
No coin nor oath required. For personal study only.
magnified image
Efficient syntheses of dibenz[b,f][1,4]oxazepin‐11(10__H__)‐one, 5,10‐dihydro‐11__H__‐dibenzo[b,e][1,4]‐diazepin‐11‐one and 5,11‐dihydro‐6__H__‐dibenz[b,e]azepin‐6‐one are described using a tandem reductionlactamization sequence. Precursors for these ring systems are available in 1‐3 steps using nucleophilic aromatic substitution and Ullmann coupling methodology. Direct reduction‐lactamization of these compounds using iron powder in acetic acid at 115° affords the target heterocycles in ≥90% yield.
📜 SIMILAR VOLUMES
## Abstract A two‐step diastereoselective synthesis of linear‐fused tricyclic nitrogen heterocycles has been developed from cyclic β‐ketoesters. The cyclization substrates are readily prepared by alkylation of the methyl 2‐oxo‐cycloalkanecarboxylates with 2‐nitrobenzyl bromide. Hydrogenation of the
## Abstract A tandem S~N~2‐Michael addition reaction has been developed for the synthesis of __cis__‐ and __trans__‐fused nitrogen and sulfur heterocycles from the __cis__ and __trans__ isomers of ethyl (±)‐(2__E__)‐3‐[2‐(iodomethyl)cyclo‐hexyl]‐2‐propenoate. Octahydro‐1__H__‐isoindole‐1‐acetic aci