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 encompasses 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 includes a topic index protecting Volumes 41-45, that are 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 help increase the worth of the series.Apart from those indexes, the current quantity includes 4 chapters spanning a variety of heterocyclic chemistry. ''1,5-Diazocines'' via Perlmutter, keeps his assurance 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 disguise reactions of 1,2,4-triazines with nucleophiles, an issue to which they bring about a lot expertise.There were huge, immense advancements in organo-boron chemistry over the past few many years, yet boron-containing heterocycles are nonetheless a bit of rareties. the sector is ripe for exploitation, and the bankruptcy in this topic by means of Terashima and Ishikura can help you during this respect.Finally, Kadaba has contributed the 1st complete assessment of the vast chemistry of 1,2,4-triazolines. This bankruptcy will supplement the sooner evaluation {Advances, quantity 37) on 1,2,3-triazolines through Kadaba, Stanovnik, and Tisler.

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Eberle and Houlihan reacted 1,3-propanediamine with the pyrroline 165 and obtained the pyrrolidinodiazocine 166 (7 1GEP2050344). Wamhoff and Materne treated the dihydrofurans 167 with 1,3-diarninopropane and isolated the elEt 0 MJ COOEt HN 166 165 167 168 R1- R3: H , M e furanodiazocine 168 (74CB1784). DeWald and L’ltalien found that cyclizing the aroylpyrazoles 169 with 1,3-diamines afforded the pyrazolodiazocines 170. Various N-substituted derivatives 170 and their imine N-oxides were prepared (74GEP2423642).

Reaction of 218 217 118 benzodiazocines 34 [R' = R2 = R4 = R6 = R7 = H; R5 = C1; R3 = H (79CPB2589), CH2C02Et(79CPB2608)l with methanolic hydrogen chloride afforded the quinazolines 219[R = H, R' = Cl(79CPB2589); R = CH2C02Et, R' = C1(79CPB2608)], whereas the homologous benzodiazepine did not undergo ring contraction (79CPB2589). %? (CH*),NH* Ph 279 R7 34 A common transformation of dibenzo- 1,5-diazocines has been reductive ring contraction into isoindoloindoles. Sternbach and co-workers reported that diazocine 138 (R, R', R3-R6 = H; R2 = C1) reacted with zinc and acetic acid to give 220 (R = R' = H, R2 = Cl), whereas the dihydro compounds 221 (R = H, Me), in the presence of sodium borohydride, afforded 220 (R = H, R' = Me,R2 = C1) and 220 (R = R' = H, R2 = Cl), respectively (66JA1077, 66JOC3356).

For the reverse of the 222 + 223 closure, see Section II,B,2). 223 222 = f)- C H, c E t ,CHO Et 224 In the only reported 1,5-diazocine ring expansion, Crombie et al. utilized the Homalium alkaloid precursor 180 (R = R' = H) (see Section II,D) as a synthon for an intramolecular transamidative ring expansion in a synthesis of the 13-membered (+)-dihydroperiphylline [225, R = (E)cinnamoyl], a natural product from Peripterygia marginata (87MI1). In this sequence [Eq. @)I, the diazocine 180 (R = R' = H) was alkylated with 1-bromo-4-chlorobutane to afford 180 [R = H, R' = (CH,),Cl].

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