4-(3-氧代丙-1-烯-1-基)苯甲腈

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3.9 g of 5'-bromo-2'-hydroxy-2-(methylsulfinyl)acetophenone, 2.2 g of p-cyanocinnamaldehyde, 50 ml of toluene and 0.1 ml of piperidine was refluxed for 4 hrs. The mixture was chilled, and the precipitate was filtered and recystallized from DMF, mp 275°-76° ; yield 1 g (20%); λ max mμ (ε) 223 (22,700), 273 (12,900), 330 (41,000); ν max 840 (m), 980 (m), 1280 (m), 1640 (m), 1660 (ms), 2240 (m) cm-1. was refluxed for 4 hrs The mixture was chilled the precipitate was filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3.9 g of 5'-bromo-2'-hydroxy-2-(methylsulfinyl)acetophenone, 2.2 g of p-cyanocinnamaldehyde, 50 ml of toluene and 0.1 ml of piperidine was refluxed for 4 hrs. The mixture was chilled, and the precipitate was filtered and recystallized from DMF, mp 275°-76° ; yield 1 g (20%); λ max mμ (ε) 223 (22,700), 273 (12,900), 330 (41,000); ν max 840 (m), 980 (m), 1280 (m), 1640 (m), 1660 (ms), 2240 (m) cm-1. was refluxed for 4 hrs The mixture was chilled the precipitate was filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7.85 g of 4-cyanocinnamaldehyde (U.S. Pat. No. 2,993,834), 11.4 g of 2'-hydroxy-3'-methoxy-2-(methylsulfinyl)acetophenone, 250 ml of toluene, and 0.5 ml of piperidine was refluxed for 3 hrs. The mixture was chilled, and the crystalline ppt. filtered, and recrystallized from toluene, mp. 274°-75°; yield 7 g (46%); λ max mμ (ε) 222 (20,600), 328 (42,500); ν max 745 (m), 845 (m), 1060 (m), 1275 (m), 1570 (m), 1595 (m), 1655 (ms), 2230 (m) cm-1. The mixture was chilled filtered recrystallized from toluene, mp. 274°-75°

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7.85 g of 4-cyanocinnamaldehyde (U.S. Pat. No. 2,993,834), 11.4 g of 2'-hydroxy-3'-methoxy-2-(methylsulfinyl)acetophenone, 250 ml of toluene, and 0.5 ml of piperidine was refluxed for 3 hrs. The mixture was chilled, and the crystalline ppt. filtered, and recrystallized from toluene, mp. 274°-75°; yield 7 g (46%); λ max mμ (ε) 222 (20,600), 328 (42,500); ν max 745 (m), 845 (m), 1060 (m), 1275 (m), 1570 (m), 1595 (m), 1655 (ms), 2230 (m) cm-1. The mixture was chilled filtered recrystallized from toluene, mp. 274°-75°

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This was prepared by reacting 6.36 g of 2'-hydroxy-5'-methyl-2-(methylsulfinyl)acetophenone with 6.36 g of p-cyanocinnamaldehyde in analogous fashion to 4-[2-(8-methoxy-4-oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitrile. The material was recrystallized from toluene, mp 249°-51°; yield 3.5g (41%) λ max mμ (ε) 219 (19,300); 278 (13,500), 339 (41,000); ν max 825 (m), 980 (m), 1235 (m), 1580 (m), 1630 (m), 1670 (s), 2240 (m) cm-1. This was prepared The material was recrystallized from toluene, mp 249°-51°

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This was prepared by reacting 6.36 g of 2'-hydroxy-5'-methyl-2-(methylsulfinyl)acetophenone with 6.36 g of p-cyanocinnamaldehyde in analogous fashion to 4-[2-(8-methoxy-4-oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitrile. The material was recrystallized from toluene, mp 249°-51°; yield 3.5g (41%) λ max mμ (ε) 219 (19,300); 278 (13,500), 339 (41,000); ν max 825 (m), 980 (m), 1235 (m), 1580 (m), 1630 (m), 1670 (s), 2240 (m) cm-1. This was prepared The material was recrystallized from toluene, mp 249°-51°

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This was prepared by reacting 11.4g of 2'-hydroxy-5'-methoxy-2-(methylsulfinyl)acetophenone with 7.85 g of p-cyanocinnamaldehyde in analogous fashion to 4-[2-(8-methoxy-4-oxo-4H-1-benzopyran-2-yl) ethenyl]benzonitrile. The material was recrystallized from toluene. mp 224°-26°; yield 6.5g (43%); λ max mμ (ε) 224 (20,600), 294 (21,900), 332 (43,500); ν max 820 (m), 980 (ms), 1080 (m), 1290 (m), 1580 (m), 1620 (s), 1645 (s), 2240 (m) cm-1. This was prepared The material was recrystallized from toluene

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This was prepared by reacting 11.4g of 2'-hydroxy-5'-methoxy-2-(methylsulfinyl)acetophenone with 7.85 g of p-cyanocinnamaldehyde in analogous fashion to 4-[2-(8-methoxy-4-oxo-4H-1-benzopyran-2-yl) ethenyl]benzonitrile. The material was recrystallized from toluene. mp 224°-26°; yield 6.5g (43%); λ max mμ (ε) 224 (20,600), 294 (21,900), 332 (43,500); ν max 820 (m), 980 (ms), 1080 (m), 1290 (m), 1580 (m), 1620 (s), 1645 (s), 2240 (m) cm-1. This was prepared The material was recrystallized from toluene

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Prepared from 3-(4-cyano-phenyl)acrolein and 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine by reductive amination with sodium cyanoborohydride. Yield: 8% of theory, Melting point: 199°-205° C. (decomp).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 3.9 g of 5'-bromo-2'-hydroxy-2-(methylsulfinyl)acetophenone, 2.2 g of p-cyanocinnamaldehyde, 50 ml of toluene and 0.1 ml of piperidine was refluxed for 4 hrs. The mixture was chilled, and the precipitate was filtered and recystallized from DMF, mp 275°-76° ; yield 1 g (20%); λ max mμ (ε) 223 (22,700), 273 (12,900), 330 (41,000); ν max 840 (m), 980 (m), 1280 (m), 1640 (m), 1660 (ms), 2240 (m) cm-1. was refluxed for 4 hrs The mixture was chilled the precipitate was filtered

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7.85 g of 4-cyanocinnamaldehyde (U.S. Pat. No. 2,993,834), 11.4 g of 2'-hydroxy-3'-methoxy-2-(methylsulfinyl)acetophenone, 250 ml of toluene, and 0.5 ml of piperidine was refluxed for 3 hrs. The mixture was chilled, and the crystalline ppt. filtered, and recrystallized from toluene, mp. 274°-75°; yield 7 g (46%); λ max mμ (ε) 222 (20,600), 328 (42,500); ν max 745 (m), 845 (m), 1060 (m), 1275 (m), 1570 (m), 1595 (m), 1655 (ms), 2230 (m) cm-1. The mixture was chilled filtered recrystallized from toluene, mp. 274°-75°

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This was prepared by reacting 6.36 g of 2'-hydroxy-5'-methyl-2-(methylsulfinyl)acetophenone with 6.36 g of p-cyanocinnamaldehyde in analogous fashion to 4-[2-(8-methoxy-4-oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitrile. The material was recrystallized from toluene, mp 249°-51°; yield 3.5g (41%) λ max mμ (ε) 219 (19,300); 278 (13,500), 339 (41,000); ν max 825 (m), 980 (m), 1235 (m), 1580 (m), 1630 (m), 1670 (s), 2240 (m) cm-1. This was prepared The material was recrystallized from toluene, mp 249°-51°