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A novel synthetic approach developed by the use of a microwave (MW) assisted one pot protocol to the synthesis of methyl-1,4-benzodiazepin-2-one-5-carboxylate (<b>2</b>) derivatives for which <i>N</i>-chloroacetylisatin was employed with an elegant success to afford the formation of 5-methyl carboxylate derivatives of 1,4-benzodiazepines from its reaction with methanolic hexamine. We have utilized MW technique in the present work in conducting the reaction of carboxylate ester derivative (<b>2</b>) with several selected primary and secondary amines <b>3</b>, <b>4</b>, <b>5</b>, <b>6</b>, <b>7</b>, and <b>8</b> which had the previous history of being biologically active in the literature, to generate the corresponding carboxamide derivatives (<b>9-14</b>).