By A.R. Katritzky
(from preface)This quantity makes a tremendous contribution to the method of up-dating previous volumes that we've got initiated. Seven of the 9 chapters are dedicated to this goal and to any extent further we intend to up-date chapters from 10 to fifteen years after their visual appeal, only if huge paintings has been performed within the region covered.Five chapters were up-dated by means of the authors of the unique chapters that seemed in previous volumes, as follows: Quinazolines, via W. L. F. Armarego (the unique bankruptcy seemed in quantity 1), 3-membered jewelry with Heteroatoms, through E. Schmitz (Volume 2), Physicochemical features of Purines, by means of J. H. Lister (Volume 6), Reis-sert Compounds, by way of F. D. Popp (Volume 9), and Pyridazines, by means of M. Tiffler and B. Stanovnik (Volume 9).Two different chapters up-date topics coated in prior volumes, yet through diversified authors: Selenium-Nitrogen Heterocycles, through I. Lalezari, A. Shafiee, and M. Yalpani, which up-dates the contribution via Bulka in quantity 2 on Selenazole Chemistry, and Pyrrolizidines, via D. J. Robins, which up-dates the contribution by way of Kochetkov and Likhosherstov in quantity 5.Finally, chapters take care of considerably new themes: Benzo[c]cin-nolines, by way of J. W. Barton, and 1, 4-Thiazines, by way of R. J. Stoodley.
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Extra info for Advances in Heterocyclic Chemistry, Vol. 24
J. Brown and J. A. Hoskins, Aust. J . Chenz. 25, 2641 (1972). 146 W. Ried, B. Heine, W. Merkel, and N . Kothe, Synthesis, 534 (1976). 14' A. Albert and G. Catterall, J. Chem. C, 1533 (1967). 14* E. Kalatzis, J . Chem. B, 96 (1969). L. J. Chinn, J. Heterocycl. Chem. 10,403 (1973). 145 30 W. L. F, ARMAREGO [Sec. 1]hept-2-ene-5,6-dicarboxylate, the nitrene added across the double bond and gave the adduct (52: R = 2-methylquinazolin-4-on-3-yl) in 5 4 % yield together with 2-methylquinazolin-4(3H)-one(24%).
98 2-Phenyl-5,6,7,8-tetrahydroquinazoline-4(3H)-thione synthesized from I-morpholinocyclohex- 1-ene and benzoylisothiocyanate. ' 99 2-Methyl5,6,7,8-tetrahydroquinazoline-4(3H)-thione was oxidized with potassium which propermanganate to 2-methyl-4-sulfo-5,6,7,8-tetrahydroquinazoline, 3H)-one on hydrolysis. 20' ' w C O , M e C0,Me (75) (76) (77) An approach toward the synthesis of simple analogs of tetrodotoxin (115) (see also Sections VI,C and VIII) involved a Diels-Alder reaction between a butadiene and a pyrimidine derivative.
Reece, J . S. Perkin I, 23 1 3 (1 974). 2 1 3 W. L. F. Armarego and P. A. S. Perkin I , 1470 (1975). W. L. F. Armarego, J . Chem. C, 1812 (1971). 2 1 5 W. L. F. Armarego and T. Kobayashi, J . Chem. SOC. C, 3222 (1971). 209 210 44 [Sec. B W . L. F. ARMAREGO X (85) (86) that the major conformer in solution was 86. 205321 axo Exo H OzNCHXOzH+ H (87) E H CH~NO, several (88) Z H CH, (89) Reduction of 5,6,7,8-tetrahydroquinazolin-2( lH)-one with sodium boro1H)-one (87) in high yield. hydride gave 3,4,5,6,7,8-hexahydroquinazolin-2( When this hexahydro compound was fused with nitroacetic acid a stereospecific cis addition of the elements of nitromethane occurred and the 8a-nitromethyl adduct 88 was formed in quantitative yield.