New Tricyclic Aryl Quinazoline Derivatives by Suzuki‐Miyaura Cross‐Coupling

A number of new deoxyvasicinone (2,3‐dihydropyrrolo[2,1‐b]quinazolin‐9(1H)‐one) and mackinazolinone (6,7,8,9‐tetrahydro‐11H‐pyrido[2,1‐b]quinazolin‐11‐one) derivatives with aryl substituents at C7/C8 and at C5 are reported. These compounds are rare representatives of their kind and were prepared in high yields by Suzuki‐Miyaura cross‐coupling reactions between 7‐bromo‐2,3‐dihydro[2,1‐b]quinazoline‐9‐(1H)‐one, 5,7‐dibromo‐2,3‐dihydro[2,1‐b]quinazoline‐9‐(1H)‐one or 8‐bromomackinazolinone and respective arylboronic acids with palladium acetate as the catalyst. The products were characterized spectroscopically and, in addition, by X‐ray crystal structure analyses in six cases. New quinazoline derivatives are prepared in high yields by single or double Suzuki‐Miyaura cross‐coupling of the rare respective brominated precursors. Six of the products are crystallographically characterized, and results of some DFT calculations of the new products are reported.