Quinazolines II. metal hydride reductions

The following sodium borohydride reductions are reported: 3‐methylquinazolium iodide (I) or its methanolate (II) → N α , N α ‐dimethyl‐α, 2‐toluenediamine; quinazoline → 3,4‐dihydroquinazoline or 1,2,3,4‐tetrahydroquinazoline (V). The following lithium aluminum hydride reductions are reported: I or II → 3‐methyl‐l,2,3,4‐tetrahydroquinazoline; quinazoline → V + N α ‐methyl‐α, 2‐toluenediamine (VI); 4 ‐ chloroquinazoline → VI; 2‐chloroquinazoline → VI; 2,4 ‐ dichloroquinazoline → V; 2‐chloro‐4‐phenylquinazo‐ line → 4‐phenyl‐3,4‐dihydroquinazoline; 2‐phenyl‐4‐chloroquinazoline → 2‐phenyl‐3,4‐dihydroquinazoline or N α ‐ benzyl‐α, 2 ‐ toluenediamine; 4 ‐ methoxyquinazoline → 4‐methoxy‐l,2‐dihydroquinazoline; 4‐phenoxyquinazoline → 4‐phenoxy‐l,2‐dihydroquinazoline; 4‐thiophenoxyquinazoline → VI.