Advances in Heterocyclic Chemistry, Vol. 50 by Alan R. Katritzky (Ed.)

By Alan R. Katritzky (Ed.)

(from preface)Volume 50 of Advances in Heterocyclic Chemistry includes 4 chapters. Howard D. Perlmutter has contributed a survey of 1,2- and 1,3-diazocines. this can be the fourth in a sequence of stories through Perlmutter» whose past surveys contain azocines (Volume 31,1982), 1,4-diazocines (Volume forty five, 1989), and 1,5-diazocines (Volume forty six, 1989). the current bankruptcy completes this therapy of 8-membered heterocycles containing nitrogen.R. E. Busby has written a bankruptcy on thiadiazines containing adjoining sulfur and nitrogen ring atoms. This bankruptcy enhances one in quantity forty four which handled sulfamides of this kind. H. Quiniou and O. Guilloton of Nantes have coated the chemistry of monocyclic 1,3-thiazines, a bunch that, unusually, has now not been reviewed comprehensively for a few years. ultimately, E. V. Kuznetsov and that i. V. Shcherbakova of Rostov collaborate with A. T. Balaban of Bucharest in a precis of the chemistry of benzo[c]pyrylium salts. This evaluation enhances the evaluation by way of a gaggle of authors below the management of Balaban who coated the chemistry of pyrylium salts in complement 2 of this sequence, which seemed in 1982.

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Triazocine 199 (R = R' = Ts) was obtained by reacting 1,2dibrornoethane with 200 (obtained from 2-chloronicotinic acid) (85MI3). q 0 198 199 200 Natsukari and co-workers were the authors of several reports involving ring closure of 2-chloroacetarnidobenzophenonehydrazones 201 (ha1 = C1) to give 1,4,5-benzotriazocinium salts 202 and benzotriazocines 203 (73JAP73-33760;73JAP73-35276;79CPB2084) (for an interesting ring contraction of these compounds, see Section IV, B,3). Shindo and co-workers R' NCOCH ha1 X C-NNR~R Ph 201 X Ph 203 202 48 HOWARD D.

PERLMUTTER Swenton and co-workers showed that uracyl-alkyne photoadducts 123 [R'= H, R2 = n-CsHI1 (82TL4207); R' = F, R2 = n-C3H7 (83JOC2337); R' = SiMe3, R2 = n-C3H7 (83JOC2337)l yield the corresponding diazo- cines 124 on treatment with trimethylsilyl chlondelhexamethyldisilazine followed by silica gel. The latter compounds afforded pyridones 125 on mixing with potassium terr-butoxide. These findings were taken as strong evidence for the intermediacy of diazocines 124 in the base-catalyzed fragmentationof 123to give 125,a mechanism that was strongly suggested by 15N and I3C labeling and kinetics studies and ruled out a Dewar pyridone-type intermediate (82TL4207; 83JOC2337).

Sec. IILA] 27 DIAZOCINES, TRIAZOCINES, TETRAZOCINES 105 104 106 107 I . Preparative Methods a. Via Cyclization. Klein ef al. prepared w-guanidino and a-ureido-aketoacids 108 (X = NH, 0; R = H, Me) from the corresponding a-aminoacids via oxazolidines. Compound 108 (R = Me, X = NH) was then cyclized to 1,3-diazocine 109, whereas 108 (R = H, X = NH, 0) was converted into diazabicyclic compounds (83LA 1623). (CHZ),C-C02H MeNp C NH 108 109 110 111 0 2H 28 HOWARD D. PERLMUTTER 112 [Sec. A 104 SCHEME 4 has been prepared by the action of water on pentamethylenediisocyanate (57JA4358, 57NKZ1416).

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