By Andre Rosowsky
Chapter I Dibenzazepines and different Tricyclic Azepines (pages 1–635): Burt Renfroe and Clinton Harrington
Chapter II Azepine Ring structures Containing jewelry (pages 637–768): George R. Proctor
Read Online or Download Chemistry of Heterocyclic Compounds: Azepines, Part 1, Volume 43 PDF
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Extra resources for Chemistry of Heterocyclic Compounds: Azepines, Part 1, Volume 43
27) to the hexahydro[l,2albenzimidazole 164 in 90% yield (41). Later, performic acid (98% formic acid plus 30% hydrogen peroxide) was reported to accomplish this same conversion in 80-90% yields (42,43). The hexahydro compound 164 was also obtained in good yield (44)via a straightforward annulative alkylation of the 2-bromoalkylbenzimidazole 165a (Fig. 22). A related, patented process (45) claims the acid-catalyzed cyclization of 165b, prepared from o-phenylene- 161 GQ H2N 163 0,a 162 [CF,CO,Hl CF,CO,H + 30% H 2 0 2 , N 164, 90%; rnp 124-125°C 40 Dibenzazepines and Other Tricyclic Azepines diamine and caprolactam, to 164 in 85% yield.
41 5,6,7-Systems R2 R2 167 166 166a 166b H NHAc 167a 167b NHAc H 222 252 66 58 R, R2 m p ("C) H N, N, H 98 108 167 HOAc. PPA. )low heat lo 14s"C Me 168, 68% 169, 66% Figure 23 (Eq. 28) gave a product having chemical and physical properties at variance with structure 171 (47). The product had an ultraviolet absorption spectrum similar to those of 2-alkylbenzimidazoles and proved to be identical with the product obtained via the decomposition of 161 (X = H). Yields of 164 from 170 were relatively poor: 21% with ferrous oxaiate as the reductant and only 15% using iron.
An oxaziridine similar to that in Fig. 29 was proposed as an intermediate leading to 188. I H 0 176 O2N I OTs Figure 29 186 Dibenzazepines and Other Tricyclic Azepines 48 TABLE 13. PRODUCTS FROM IRRADIATION OF BENZIMIDAZOLE N-OXIDES 1 8 7 R Product Yield (7%) H 187 188 189 187 188 190 42 25 32 12 44 CI “Eq. 30. I 188 0 (30) 187 + R ~Q+Meo c1 N 189 191 N 190 193 192 + 195, mp 144°C 194 Figure 30 IV. 49 5,6,7-Systems Anils derived from o-pyrrolidinoaniline and a wide variety of aldehydes were found to undergo a rapid acid-catalyzed cyclization in the cold to give dihydrobenzimidazoles (57).