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

By Andre Rosowsky

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

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

Example text

When the reagent is one that provides a good potential leaving group, and a strong nucleophile is added as well, the reaction represents a general synthesis of substituted benzimidazoles from their N-oxides. Thus, treatment of the N-oxide 176 (Fig. 28) with benzoyl chloride and potassium cyanide gave a mixture of the 4-cyano derivative 180a and the asubstituted product 179 (X = BzO). When benzoyl chloride was replaced with tosyl chloride, only 180a was isolated. With thiocyanate ion as the nucleophile, a higher yield of 180b was obtained.

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. CYANINE DYES FROM THIAZOL0[2,3-b][2]- AND [3,2B][2]BENZAZEPlNES Me 1 1 CMe, Me 234 1 I I 2 2 1 S CH=CH Et Et 237 243 0 CMe, Me 246 0 S Et 243 TABLE 7. 534 556 600 505 565 BIS-CYANlNE DYES FROM THlAZOLO[2,3-h] [ 3 ] AND [3,2-h] [ZIBENZAZEPINES CIO; Me Ph H Me Ph Ph H H H H H Ph Ph H H Me Me Ph 31 174 140-14 1 196 146 174 212 205 190 580 610 599 606 613 620 643 680 686 32 Dibenzazepines and Other Tricyclic Azepines 12.

Whether the reaction yields 177 or 176 apparently depends on a combination of steric and electronic factors. Mechanisms involving photoexcitation of the nitro group to a diradical (which may attack the methylene group adjacent to the tertiary amine nitrogen to give 176 or react with the basic nitrogen itself to form 177) are discussed in a full paper (52). Suschitzky and Meth-Cohn have reported the nuclear substitution of benzimidazole N-oxides with concomitant loss of the N-oxide functionality (54, 55).

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