New PDF release: Chemistry of Heterocyclic Compounds: Azepines, Part 1,

By Andre Rosowsky

ISBN-10: 0470187212

ISBN-13: 9780470187210

ISBN-10: 0471018783

ISBN-13: 9780471018780

Content material:
Chapter I Dibenzazepines and different Tricyclic Azepines (pages 1–635): Burt Renfroe and Clinton Harrington
Chapter II Azepine Ring platforms Containing earrings (pages 637–768): George R. Proctor

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Extra resources for Chemistry of Heterocyclic Compounds: Azepines, Part 1, Volume 43

Example text

In each instance, there was a bathochromic shift of 50-60 nm in the A,, relative to the unsubstituted open-chain thiazolocyanines. 128 129 132 Dibenzazepines and Other Tricyclic Azepines 30 131 130 133 Me lMa, rn = n = I ; mp 216°C (A,,,468 nm) 134b, r n = 2, n = O ; mp 156°C (A,,,446 nm) TABLE 5 . RI 135, mp 215°C (A,,,568 DERIVATIVES OF THIAZOL0[2,3-b][3]- AND [3,2-b][2]BENZAZEPINES RZ rn n mp [3,2-b1[2]series H Me Et Ph Ph Ph H H H H Me Ph 1 I 1 1 1 1 192- 193 235-236 97-98 198 210-21 1 212 [2,3-b1[3] series H Me Ph H H H 2 2 2 203-204 159-160 169- 170 nm) TABLE 6.

5. Oxazolo[2,3-a][2]benzazepines Single examples of both the oxazolo[2,3-a]benzazepinesystem and the corresponding thiazolo system (Section IV. 9) were prepared (19) by stirring the bromoaldehyde 102 at ambient temperature in dioxane with one equivalent of ethanolamine or mercaptoethylamine (Fig. 14). Physical constants for the products are listed in Table 3. The intermediate Schiff base presumably quaternizes to give 103. The free hydroxy or mercapto group then adds to the imrnonium bond, forming 104.

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.

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Chemistry of Heterocyclic Compounds: Azepines, Part 1, Volume 43 by Andre Rosowsky


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