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

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NaCIO, 137 138, 74%; mp 195-196°C 13. 139 Azepino[2,1-b]benzoselenazoles An example of the azepino[2, I-h]benzoselenazole system, 141, has been prepared in modest yield (21), as shown in Eq. 20, by the addition of dimethyl acetylenedicarboxylate to 2-methylbenzoselenazole (140). The reaction of similar substrates with acetylene dicarboxylic esters has been a TABLE 8. CYANINE DYE DERIVATIVES OF T H I A Z O L O [ ~ , ~ - U 11BENZAZEPINES ][ 74 179 600 52 181 525 41 I92 530 43 200 560 64 185 602 61 164 444 79 215 574 I CH, CH I CH 0 I 33 Dibenzazepines and Other Tricyclic Azepines 34 WFMe ' MeO,C---CO,Me Se , 140 (20) 141, mp 214°C (yellow) source of other, related heterocycles.

16. DMF M e 0e o m S 0 2 M e ( 1 ) HOCH2CH20H Me0 9. Thiazolo[2,3-~][21benzazepines (2) Raney NI (3) H' ' 124 IV. 5. 10. Thiazolo[2,3,-b][3]benzazepines 11. Thiazolo[3,2-b][2lbenzazepines These two closely related isomeric ring systems have been investigated as part of a broad search for new cyanine dyes (28). As shown in Eq. 17, 2,3-disubstituted 10,l l-dihydrothiazolo[3,2-b][2]benzazepinium perchlorates (132)can be prepared from 2-benzazepin-3-thione (129)by annulation with a-bromoketones. Likewise, 2-substituted derivatives (133)of the isomeric 5,6-dihydro[2,3-b][3] ring system can be prepared from 3-benzazepin2-thione (130)(Eq.

23 and 24 were converted in good yields to the azides 154 and 156, which were not characterized but were thermally decomposed in nitrobenzene to give the [3’,2’:4,5]isomer 155 and the [3’,4’:4,5]isomer 157 in 15 and 72% yield, respectively (37). The lower yield of 155 may have been due to an unstable diazonium intermediate. Regardless of whether the reactive intermediate in the azide decomposition is an electrophilic (RN:) or biradical (RN:) species, it probably combines with a methylene group of the hexahydroazepine to form an unstable dihydro intermediate such as 158 (Eq.

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