Advances in Heterocyclic Chemistry, Vol. 46 by Alan R. Katritzky

By Alan R. Katritzky

(from preface)Volume forty six of Advances in Heterocyclic Chemistry is an ''Index Volume.'' It features a cumulative index of the titles of articles that have seemed within the sequence (Volumes 1-45), and a cumulative index of authors who've written those contributions. also it features a topic index overlaying Volumes 41-45, which might be utilized in conjunction with the topic index in quantity forty (which covers Volumes 1-40). it truly is was hoping that the availability of those indexes may also help increase the price of the series.Apart from those indexes, the current quantity includes 4 chapters spanning a variety of heterocyclic chemistry. ''1,5-Diazocines'' by means of Perlmutter, keeps his insurance of vital 8-membered heterocycles (cf. ''Azocines'' in quantity 31, and ''1,4-Diazocines'' in quantity 45). Charushin, Alexeev, and Chupahkin from the Soviet Union, and Van der Plas from Holland conceal reactions of 1,2,4-triazines with nucleophiles, a subject matter to which they create a lot expertise.There were huge, immense advancements in organo-boron chemistry over the last few many years, yet boron-containing heterocycles are nonetheless a bit rareties. the sector is ripe for exploitation, and the bankruptcy in this topic by way of Terashima and Ishikura may help during this respect.Finally, Kadaba has contributed the 1st accomplished evaluation of the wide chemistry of 1,2,4-triazolines. This bankruptcy will supplement the sooner overview {Advances, quantity 37) on 1,2,3-triazolines by way of Kadaba, Stanovnik, and Tisler.

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The isoxazoline 125 (R = OMe), when heated, rearranged to yield methyl N-ethylanthranilate and diazocine 35 (R = R' = Et) (71JA1543). 122 123 124 125 A number of heterocycle-fused 1,5-diazocines have been reported. Klisiecki and Sucharda treated an ethyl acetate solution of methyl nicotinate with sodium and obtained diazocine 126 (23RC251). In a more recent, but similar, report, Oakes and Rydon attempted a Claisen condensation of ethyl 3-aminopicolinate with ethyl acetate, but obtained instead the intermolecular amidation product 127 (58JCS205).

C HOWARD D. PERLMUTTER 149 S CNC (Me) 2CH,COCHS ( yPhN - Me 150 e 151 (83S830). Use of the N-nitro derivative 152 (R = NO,) gave the N-nitrodiazocines 153 (R = NO, ;R' = H, Me) (838830). There have been two reports of reaction of N-methyl-p-toluidine with acidic formaldehyde solution to yield the diazocine 67 (R'-R3 = H, R4 = RS = Me) (76CI(L)1644). Similarly, reaction of formaldehyde with diphenylamine afforded [ RN CH,CH(NO,)~ 152 I, 153 diazocine 67 (R'-R3 = H, R4 = R5 = Ph) (78GEP2729363). Kutlu condensed saccharin and paraformaldehyde with 0-,m-, and p-aminophenols and obtained diazocines 154,155, and 156, respectively (70MI2).

Llnonane (201) with formaldehyde (66DIS406B); the condensation of cis- and trans-dibenzodiazocines 202 to yield the diastereomeric methano compounds 203 (66JOC3356); and imine reduction of 18 (R = R' = H) (see Section II,A,2), followed by reaction with formaldehyde, to afford 200 (R = Ph, R' = H) (77FES33). Diazocine C-C bridging was accomplished when dibenzodiazocinediiR 102 200 0' Ph CI 201 ' Ph / H 202 Ph Ph 203 50 HOWARD D. PERLMUTTER [Sec. A 2 05 204 206 minium salt 204 (R = Me) was hydrolyzed in aqueous methanol to afford the 6,12-epoxy compound 205 (67JHC435).

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