Synthesis of quinazolinophanes containing bridgehead nitrogen atoms from quinazoline‐2,4(1H, 3H)‐dione

Abstract

Quinazoline-2,4(1H,3H)-dione (1) reacts with , -dihaloalkanes to generate three types of quinazolinophanes. When the number of carbon atoms in the dihaloalkanes is 9, a mixture of all the three types of quinazolinophanes (2), (3) and (4) was produced; and when the number of carbon atoms in the dihaloalkane used is from 4 to 7, a mixture of only two types of quinazolinophanes (2) and (3) were produced. When the number of carbon atoms of the dihaloalkane used is odd (5, 7 and 9), the different structural types of quinazolinophanes produced were easily identifiable and distinguishable on the basis of 13 C NMR and mass spectral data.