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Get Chemistry of Heterocyclic Compounds: Azepines, Part 2, PDF

By Andre; Renfroe, Burt; Watthey, Jeffrey W. H. Rosowsky

ISBN-10: 0470187220

ISBN-13: 9780470187227

ISBN-10: 047189592X

ISBN-13: 9780471895923

Dibenzodiazepines and different Tricyclic Diazepine platforms (J. Watthey & J. Stanton).

Monocyclic and Condensed Triazepines and Tetrazepine (N. Peet).Content:
Chapter I Dibenzodiazepines and different Tricyclic Diazepine structures (pages 1–717): Jeffrey W. H. Watthey and James L. Stanton
Chapter II Monocyclic and Condensed Triazepines and Tetrazepines (pages 719–842): Norton P. Peet

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Additional resources for Chemistry of Heterocyclic Compounds: Azepines, Part 2, Volume 43

Example text

OR 91 92 93 (nmr, ir, uv) Alternatively, 3-alkoxyhalides could be used instead of 3-chloropropanol. Again, cyclization was achieved with 48% hydrobromic acid. Reaction of 91 with 1-bromo-3-chloropropane and sodium hydroxide in dimethylformamide gave 93 directly. Substances functionalized on the 3-carbon bridge were prepared by analogous procedures (Fig. 5 ) . These studies were later extended to the preparation of nitro derivatives (53) (Eq. 22, Fig. 6). The pivaloate 101 was prepared from the hydroxy compound with pivaloyl chloride.

3. Diazotization of 49 followed by addition of ethyl 2-chloroacetoacetate led to azo compound 50. Addition of ammonia to 50 followed by reaction with chloroacetyl chloride generated 52. Acid-catalyzed cyclization of 52 to give 53 completed the synthesis of the triazole. Ring closure of 53 to diazepine 54 was effected with hexamethylenetetramine. Use of methanolic ammonia led to concomitant formation of the corresponding carboxamide. Treatment of 54 with rn-chloroperbenzoic acid led to the N4oxide 55, which could also be prepared directly from 53 by reaction with hydroxylamine (32,33).

Cleavage of the diazepine ring to 64 was accomplished with 10% aqueous hydrochloric acid followed by sodium nitrite. Reaction of 64 with amines led to the adducts 67. On treatment with aqueous potassium carbonate, 64 was converted to alcohol 65. In refluxing formic acid and formaldehyde, 61 was transformed to dimethylamino derivative 66. Ring-opened compounds of this class are listed in Table 11 (30,44). Other reactions of the basic tricyclic system (Eq. 16) included nitration of 73 to yield 74 (34) and photolysis of 75 to give the acetyl derivative 76 (38,45).

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Chemistry of Heterocyclic Compounds: Azepines, Part 2, Volume 43 by Andre; Renfroe, Burt; Watthey, Jeffrey W. H. Rosowsky


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