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

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

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

Monocyclic and Condensed Triazepines and Tetrazepine (N. Peet).Content:
Chapter I Dibenzodiazepines and different Tricyclic Diazepine platforms (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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Extra resources for Chemistry of Heterocyclic Compounds: Azepines, Part 2, Volume 43

Sample text

The compounds prepared by these methods are summarized in Table 14 (29,30). These diazepines undergo hydrolysis of the imine bond to give the substituted thiophenes 115 (Eq. 25). Hydrolysis with aqueous hydrochloric acid generated the intermediate amino ketones (115, Y = NH,), which were converted directly to the corresponding chlorides (115, Y = C1) by addition of sodium nitrite to the acidic reaction mixture. With sulfuric acid, the nitrite procedure converted 114 to the corresponding alcohols 115 (Y = OH).

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. The position of the double bond in 104 was determined on the basis of the nmr spectrum. Compounds 99 and 103 demonstrated significant antiprotozoal activity. Dibenzodiazepines and Other Tricyclic Diazepine Systems 40 dil. HCI rnp 158-160°C (uv, ir) 94, CH20H I CHOH Cl 95, mp 239-241°C (uv, ir) I 96, mp 150-152°C A 97, mp 156-158°C (uv, ir, nmr) Figure 5 93 HNO,/Ac2O/AcOH 98, mp 300” 99, mp 266-267°C V .

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). In addition, the Hunsdiecker reaction with 77 led to bromothiophene r H N O,IH,SO, 73, 15, 77, R R R = = = H Et H02C 74 76 I I I 78 35 V. 5,5,7-Systerns derivative 78. Compounds synthesized by this process are included in Table 7 (46). Turning to reactions at the 1-position (Eq.

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