Efficient Synthesis of 2,3,4,5-Tetrahydro-1H-3-benzazepines by Intramolecular Heck Reaction

Stereoselective synthesis of N-heterocycles: application of the asymmetric Cu-catalyzed addition of Et2Zn to functionalized alkyl and aryl imines

“…Moreover, no product resulting from an iodine-zinc exchange was observed. 25 Finally, reaction with allyl bromide 26 afforded compounds 34 and 35 in 97% and 85% yields, respectively (Scheme 10).…”

“…General procedure for the synthesis of the sulfinic acid adducts 8, 10, 12,14,26,30 Aldehyde (6.1-20.0 mmol, 1.5 equiv) was mixed with P,Pdiphenylphosphinic amide (6) (4.0-13.3 mmol, 1 equiv) and p-toluenesulfinic acid (6.1-20 mmol, 1.5 equiv) in Et 2 O (41-140 mL). The resulting mixture was then stirred at rt for 24-48 h. The white precipitate was then filtered through a fine sintered funnel and washed with Et 2 O to give sulfinic acid adduct as a white solid.…”

“…The general procedure 26 was followed using chiral amine (0.87-1.1 mmol), K 2 CO 3 (150-191 mg, 1.1-1.4 mmol), KOH (147-187 mg, 2.6-3.3 mmol), NBu 4 $HSO 4 (30-38 mg, 0.09-0.1 mmol), distilled allyl bromide (100-120 mL, 1.1-1.4 mmol) in PhMe (11-14 mL) at 60 C for 5-13 h. The crude material was purified by flash chromatography on silica gel to afford the allylic amine. RuH(CO)(PPh 3 ) 3 (10 mg, 0.010 mmol) was added to a solution of 34 (300 mg, 0.75 mmol) in PhMe (38 mL).…”

Distinguishing rotamers in N‐trifluoroacetyl‐3‐benzazepine derivatives

“…Compounds 1 and 3–7 were synthesized using literature procedures . Compound 2 was prepared following a strictly analogous sequence but employing a 2:1 molar ratio of ICl in the iodination of N ‐trifluoroacetyl‐2‐(3‐methoxyphenyl)ethanamine, giving N ‐trifluoroacetyl‐2‐(2,4‐diiodo‐5‐methoxyphenyl)ethanamine that was then treated with allyl bromide to afford 2 .…”

Regioselective alkylation of 1,3,4,5-tetrahydrobenzo[d]azepin-2-one and biological evaluation of the resulting alkylated products as potentially selective $$\hbox {5-HT}_{\mathrm{2C}}$$ 5-HT 2 C agonists

“…The preparation of C-1-substituted 3-benzazepin-2-one derivatives has been reported in the literature by cyclizing the pre-substituted acyclic derivatives into the desired azepines using a Heck reaction and other cyclization methods [27][28][29]. However, these methods use drastic reaction conditions with or without metallic catalysts offering poor yields (30-60 %).…”