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(4Z)-1-Propargyl(1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one

1
Laboratoire de Chimie Organique Hétérocyclique , Faculté des Sciences, Avenue Ibn-Batouta, Rabat, Maroc
2
Blood-Brain Barrier Laboratory (EA 2465), IUT of Béthune, University of Artois, BP 819, 62408 Béthune, France
*
Author to whom correspondence should be addressed.
Molbank 2006, 2006(5), M498; https://doi.org/10.3390/M498
Submission received: 18 July 2006 / Accepted: 20 July 2006 / Published: 1 September 2006
We describe in this work the synthesis of new benzodiazepine derivatives susceptible to possess various pharmacological activities.
Molbank 2006 m498 i001
To a solution of (4Z) -2-oxopropylidene-1,5-benzodiazepin-2-one 1[1,2] (0,01 mole, 2,16 gm in tetrahydrofuran 60 mL, was added K2CO3 (0.02mole, 2,76 gm), propargylbromid (0,02 mole, 2,36 gm) and tetra n-butylammonium bromid TBAB (0,001 mole, 0,321 gm). The mixture was stirred at room temperature for 48 hours. The solution was filtered by suction filtration. The solvent was removed under reduced pressure. The residue was chromatographed on silica gel column using hexane and ethyl acetate (80/20) as eluent to afford the products 2a and 2b as white solids.
(4Z)-1-Propargyl-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one, 2a
This compound was obtained in 50% yield;
Melting Point: 172-174 °C
1H-NMR (250 MHz, CDCl3): δ= 2.1 (s,3H,CH3),2.3(t,1H,4J=2.4 Hz, Molbank 2006 m498 i002), 3.1(HAHB, J=11.8 Hz, Molbank 2006 m498 i003), 4.7(HAHB, 2J=17.17 Hz, 4J=2.4 Hz, Molbank 2006 m498 i004 ), 5.3(s,1H, Molbank 2006 m498 i005),7.1-7.3(m, 4H, HArom)
13C-NMR (62.9 MHz, CDCl3): δ= 29.4, 38.5, 41.2, 72.5, 79.0, 96.6,122.6, 123.2, 125.6, 126.7, 132.4, 134.5, 155.0, 166.7, 198.1
Elemental analysis: Calculated for C15H14N2O2: C, 70.85 %; H, 5.55 %; N, 11.02 %; Found: C, 70.67 %; H, 5.46 %; N, 11.13 %;
(4Z)-1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one, 2b
This compound was obtained in 25% yield;
Melting Point: 173-176 °C
1H-NMR (250 MHz, CDCl3): δ= 1.9(t, 1H, 4J=2.6 Hz, Molbank 2006 m498 i006), 2.1 (s,3H,CH3), 2.3 (t,1H, 4J=2.4 Hz, Molbank 2006 m498 i007), 3.3 (t, 1H, 4J=7 Hz, Molbank 2006 m498 i008), 4.2(HAHB, 2J =17.4 Hz, Molbank 2006 m498 i009),4.7 (d,2H,2J=2.5 Hz, Molbank 2006 m498 i010),5.21(s,1H, Molbank 2006 m498 i011),7.1-7.3(m,4H, HArom), 12.6(s,1H,NH).
13C-NMR (62.9 MHz, CDCl3): δ= 16.0, 29.9, 38.6, 44.7, 93.5 122.7, 123.3, 125.8, 125.8, 127.0,131.9 134.2, 156.2, 166.9, 198.1
Elemental analysis: Calculated for C18H16N2O2: C, 73.95 %; H, 5.52 %; N, 9.58 %; Found: C, 73.82 %; H, 5.58 %; N, 9.66 %;

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

References

  1. El Abbassi, M.; Essassi, E.M.; Fifani, J. Tetrahedron Lett. 1987, 28, 1389.
  2. Djerrari, B.; El Abbassi, M.; Essassi, E.M.; Fifani, J. Tetrahedron Lett. 1989, 30, 7069.

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MDPI and ACS Style

Said, O.M.S.M.; Rachid, B.; Joly, N.; Lequart, V.; Martin, P.; Massoui, M.; Essassi, E.M. (4Z)-1-Propargyl(1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one. Molbank 2006, 2006, M498. https://doi.org/10.3390/M498

AMA Style

Said OMSM, Rachid B, Joly N, Lequart V, Martin P, Massoui M, Essassi EM. (4Z)-1-Propargyl(1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one. Molbank. 2006; 2006(5):M498. https://doi.org/10.3390/M498

Chicago/Turabian Style

Said, Ould Mohamed Sidya Mohamed, Bouhfid Rachid, Nicolas Joly, Vincent Lequart, Patrick Martin, M. Massoui, and El Mokhtar Essassi. 2006. "(4Z)-1-Propargyl(1,3-Dipropargyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one" Molbank 2006, no. 5: M498. https://doi.org/10.3390/M498

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