Advances in Heterocyclic Chemistry, Vol. 24 by A.R. Katritzky

By A.R. Katritzky

(from preface)This quantity makes a tremendous contribution to the method of up-dating previous volumes that we have got initiated. Seven of the 9 chapters are dedicated to this objective and any further we intend to up-date chapters from 10 to fifteen years after their visual appeal, only if massive paintings has been conducted within the sector covered.Five chapters were up-dated via the authors of the unique chapters that seemed in past volumes, as follows: Quinazolines, through W. L. F. Armarego (the unique bankruptcy seemed in quantity 1), 3-membered earrings with Heteroatoms, by means of E. Schmitz (Volume 2), Physicochemical facets of Purines, by means of J. H. Lister (Volume 6), Reis-sert Compounds, by way of F. D. Popp (Volume 9), and Pyridazines, via M. Tiffler and B. Stanovnik (Volume 9).Two different chapters up-date topics lined in prior volumes, yet by means of assorted authors: Selenium-Nitrogen Heterocycles, by means of I. Lalezari, A. Shafiee, and M. Yalpani, which up-dates the contribution by way of Bulka in quantity 2 on Selenazole Chemistry, and Pyrrolizidines, via D. J. Robins, which up-dates the contribution by means of Kochetkov and Likhosherstov in quantity 5.Finally, chapters take care of considerably new subject matters: Benzo[c]cin-nolines, by way of J. W. Barton, and 1, 4-Thiazines, by way of R. J. Stoodley.

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Cata~~ lytic reduction of 5,6,7,8-tetrahydroquinazolineswith Pd/C in the presence of acid ceased after absorption of 1 mol equivalent of hydrogen, and gave 3,4,5,6,7,8-hexahydroquinazoline as the hydrochloride. The hexahydro compound, in chloroform solution, was slowly oxidized by air to the starting material. ’” The catalytic reduction (Pt02-AcOH) of 2-amino-4carboxy-5,6,7,8-tetrahydroquinazoline and 4-carboxy-5,6,7,8-tetrahydroquinazolin-2( 1H)-one (or their methyl esters) similarly occurred across the 3,4 double bond, and gave the corresponding 3,4,5,6,7,8-hexahydroquinazolines.

Hirobe, and T. Okamoto, Yukuguku Zusshi 94,945 (1974). 1 6 5 E. Hayashi, T. Higashino, and S. Tomisaka, Yukuguku Zusshi 87, 578 (1967). Sec. V] 33 QUINAZOLINES The addition of Michael reagents to quinazoline 3-oxide was studied in great detail by Higashino, Hayashi, and their collaborators. Ketones with an a-methylene group, in the absence of a base, added across the 3,4-doublebond of quinazoline 3-oxide, but the reaction proceeded further; ring cleavage, elimination of hydroxylamine, and the 2-carbon atom followed, and the corresponding 2,3-disubstituted quinolines were obtained [Eq.

VI. Reduced Quinazolines Quinazolinones and thiones are not considered as hydro compounds in this section unless other double bonds in the rings are saturated. 4-Methylene3,4-dihydroquinazolines, however, are included in this section. A. 1,2-, 1,4-, A N D 3,4-DIHYDROQUINAZOLINES A new ring closure to quinazolines was found by allowing 2-benzoyl-5nitroaniline to react with hexamine (hexamethylenetetramine),in the presence of ethyl or-bromoacetate, in a solvent. When the solvent was methanol, M.

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