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Synlett

Volumn , Issue 7, 2007, Pages 1106-1108

A new strategy for pyrrolo[l,2-a][l,4]diazepine structure formation

(5) Stroganova, Tatyana A a Butin, Alexander V a Vasilin, Vladimir K a Nevolina, Tatyana A a Krapivin, Gennady D a

a KUBAN STATE TECHNOLOGICAL UNIVERSITY (Russian Federation)

Author keywords

Furan; Pyrrolo 1,2 a 1,4 diazepinone; Ring closure; Ring opening

Indexed keywords

DIAZEPINE DERIVATIVE; PYRROLO[1,2 A][1,4]DIAZEPINE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; RING CLOSING METATHESIS; RING OPENING;

EID: 34248191714 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-977430 Document Type: Article

Times cited : (33)

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40
- 34248174245
- General Procedure for the Preparation of Compounds 2a,b To a stirred solution of 5-methylfurfurylamine (12 mmol) in anhyd benzene (30 mL) a solution of 2-nitrobenzoyl or 2-nitroveratroyl chloride (10 mmol) in benzene (30 mL) was added dropwise over 30 min. The reaction mixture was agitated at r.t. for an additional 1 h and then cold sat. aq Na2CO3 (50 mL) was added. The organic layer was separated, washed with H2O, dried over Na2SO4 and concentrated in vacuo. The residue was crystallized from PE-CH2Cl2. Selected analytical data for 2b: mp 166-167 °C. IR: vmax, 3260, 1642, 1580, 1519, 1339, 1289, 1267, 1226, 1052, 994, 872, 789 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.28 (s, 3 H, CH3, 3.96 (s, 3 H, OCH3, 3.97 (s, 3 H, OCH3, 4.58 (d, 2 H, J, 5.3 Hz, CH2, 5.85 d, 1 H, J, 3.0 Hz, HFur
- 6: C, 56.25; H, 5.03; N, 8.75. Found: C, 56.12; H, 5.09; N, 8.80.

41
- 34248207081
- General Procedure for the Preparation of Compounds 3a,b A mixture of amide 2a,b (4.3 mmol, hydrazine hydrate (1.5 mL) and activated Raney nickel (1.0 g) in EtOH (60 mL) was refluxed for 10-20 min until complete conversion of 2a,b (TLC, The mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure. The residue was decolorized with charcoal in EtOAc-PE solution. The solvent was removed in vacuo and the resulting product was recrystallized from PE-CH2Cl2 to afford amino amides 3a,b. Selected analytical data for 3b: mp 125-126 °C. IR: vmax, 3373, 3293, 1629, 1592, 1535, 1509, 1453, 1361, 1262, 1209, 1171, 1104, 1024, 887, 829, 780 cm1. 1HNMR (300 MHz, CDCl3, δ, 2.29 (s, 3 H, CH 3, 3.82 (s, 3 H, OCH3, 3.86 (s, 3 H, OCH3, 4.53 (d, 2 H, J, 5.3 Hz, CH2, 5.42 (br s, 2 H, NH 2, 5.92 d
- 4: C, 62.06; H, 6.25; N, 9.65. Found: C, 62.14; H, 6.19; N, 9.60.

42
- 34248138327
- General Procedure for the Preparation of Compounds 5a,b A mixture of amino amide 3a,b (2 mmol, glacial AcOH (10 mL) and coned HCl (1.5 mL) was kept at 60-70 °C until complete conversion of the initial compounds (TLC, The reaction mixture was poured into iced H20 (100 mL) and neutralized with NaHCO3 to approximately pH 7. The precipitate thus obtained was filtered off, washed with H2O, air-dried and dissolved in EtOAc-PE. The solution was passed through a pad of silica gel and left for crystallization. Selected analytical data for 5b: mp 195-196 °C. IR: vmax, 3189, 1652, 1609, 1514, 1458, 1256, 1213, 1127, 1040, 1017, 926, 872, 799 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.34 (s, 3 H, CH3, 3.93 (s, 3 H, OCH3, 3.96 (s, 3 H, OCH3, 4.08-4.13 (m, 2 H, CH2, 5.99 (d, 1 H,J, 3.2 Hz, HPyr, 6.02 d, 1 H, J, 3.2 H
- 3: C, 66.16;H, 5.92; N, 10.29. Found: C, 66.10; H, 5.99; N, 10.23.

43
- 34248147405
- General Procedure for the Preparation of Compounds 7a-c To a suspension of pyridinethione 6 (10 mmol) in EtOH (75 mL) KOH (10 mmol, 10% aq soln) was added and the reaction mixture was heated until the complete dissolution of 6. Chloroacetamide was added and, after 15 min, the mixture was treated with a further portion of KOH (10 mmol, 10% aq soln, The solution thus obtained was allowed to stand for 2 h at r.t. The mixture was quenched with H2O (25 mL) and the precipitate formed was separated by filtration. The crystals were dried and recrystallized from EtOH-DMF (10:3, Selected analytical data for 7c: mp 77-78 °C. IR: vmax, 3404, 3313, 3241, 1657, 1594, 1544, 1501, 1417, 1305, 1294, 1269, 1218, 1198, 1186, 1155, 1088, 1071, 1016, 918, 865, 799, 752, 705 cm-1. 1H NMR (300 MHz, CDCl3, δ, 2.24 (s, 3 H, CH 3, 2.57 (s, 3 H, CH3, 3.38 (s, 3 H, OCH3, 4.34 d, 2
- 3S: C, 59.11; H, 5.54; N, 12.17. Found: C, 59.17; H, 5.49; N, 12.21.

44
- 0010169390
- Kaigorodova, E. A.; Konyushkin, L. D.; Mikhailichenko, S. N.; Vasilin, V. K.; Kul'nevich, V. G. Khim. Geterotsikl. Soedin. 1996, 1432.
- (1996) Khim. Geterotsikl. Soedin , pp. 1432
- Kaigorodova, E.A.¹ Konyushkin, L.D.² Mikhailichenko, S.N.³ Vasilin, V.K.⁴ Kul'nevich, V.G.⁵

45
- 34248155625
- Compounds 8a-c were prepared from 6a-c similarly to 5a,b (see ref. 17, Selected analytical data for compound 8c: mp 240-241 °C. IR: vmax, 3168, 1640, 1584, 1549, 1527, 1517, 1345, 1267, 1255, 1213, 1198, 1155, 1109, 942, 859, 804, 777, 752 cm-1. 1HNMR (300 MHz, DMSO-d6, δ, 1.93 (s, 3 H, CH3, 2.65 (s, 3 H, CH3, 3.23 (s, 3 H, OCH3, 4.13 (d, J, 13.2 Hz, 1 H, CH2, 4.15 (d, J, 5.2 Hz, 2 H, CH2, 4.48 (d, J, 13.2 Hz, 1 H, CH2, 6.10 (s, 2 H, HPyr, 7.45 (s, 1 H, HPy, 8.72 (t,J, 5.2 Hz, NH, 13C NMR (50 MHz, CDCl3, δ, 13.1, 24.0, 37.7, 58.2, 69.0, 105.7, 109.8, 120.0, 123.4, 128.3, 129.3, 129.6, 134.4, 144.1, 158.2, 158.7, 163.5. MS: m/z, 327 (100, M, 312 (11, 284 (10, 283 (84, 280 (32, 268 (18, 267 (14, 266 20, 253
- 2S: C, 62.37; H, 5.23; N, 12.83. Found: C, 62.30; H, 5.29; N, 12.89.

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