RESEARCHES ON QUINAZOLINES (FIFTEENTH PAPER¹). ON A 3-AMINOQUINAZOLINE, AND THE CORRESPONDING 3,3'-DIQUINAZOLYL, FROM 6-NITROACETANTHRANIL AND HYDRAZINE HYDRATE.²

Abstract

The preparation of quinazolines from 6-nitroacetanthranil and primary monamines has been reported from this laboratory in previous papers,3 the reactions involved being as follows:N-COCH, CO N-C-CH.

A REVIEW OF SOME RECENT INVESTIGATIONS IN THE QUINAZOLINE GROUP.2

“…/\ /w\ N V N (i, 3,6,8-N aphthotetrazine) NVVVN (1,3,7, and in this were equally fortunate. Naphthotetrazines of both types were prepared from the bis-acylanthranils of the appropriate diaminophthalic acid and various primary These acids, as can be seen by a glance at their graphic formulas, are only double anthranilic acids, and undergo similar reactions, the former yielding the 1,3,6,8-naphthotetrazines, and the latter the 1,3,7,9-isomers.…”

“…6 Bischler and Burkart, Ber., 26, 1349 (1893). 7 Anschutz, Schmidt and Greiffenberg, Ber., 35, 3480 (1902). By these various methods, we prepared 5-nitro-,1 6-nitro-,2 and 7-nitro-4-quinazolones.8 Of the four possible types of benzoylnitroquinazolines, representatives of the 6-nitro,4 and 8-nitro,5 were already known.…”

“…The particular quinazolines described in the foregoing are for the most part of the type designated as 4-ketodihydroquinazolines or, more simply, 4-quinazolones, (8) (NI} (7)(^\/ ^C -R (2) <6U\ i-R(3)…”