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Short Note

(4Z)-1-Benzyl (1,3-Dibenzyl)-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), M499; https://doi.org/10.3390/M499
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 m499 i001
To a solution of 4Z-2-oxopropylidene)-1,3,4,5-tetrahdro-2H-1,5-benzodiazepin–2-one 1[1,2] in tetrahydrofuran (60mL), was added K2CO3 (0,02 mole, 2,76 gm), benzylchlorid (0,02 mole, 2,52 gm) and n-tetrabutylammonium bromid (0.001 mole, 0,321 gm). The mixture was stirred at room temperature for 48 hours. The soultion was filtered by suction filtration. The solvent was removed under reduced pressure. The residu 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-benzyl-4-oxopropylidene)-1,3,4,5-tetrahdro-2H-1,5-benzodiazepin–2-one, 2a

This compound was obtained in 55% yield;
Melting Point: 165-167 °C
MS(IE):M.+ m/z=306
1H-NMR (250 MHz, CDCl3): δ= 2.1 (s,3H,CH3), 3.13(HAHB,, 2J=15.47 Hz, Molbank 2006 m499 i002), 5.0 (s,2H, Molbank 2006 m499 i003), 5.3 (s,1H, Molbank 2006 m499 i004),7.1 -7.3(m, 4H, HArm), 12.2(s,1H,NH).
13C-NMR (62.9 MHz, CDCl3): δ= 29,.5, 41.4, 52.2 , 96.5, 123.2, 123.4, 125.5, 126.6, 126.7, 127.3, 128.7, 132.9, 134.7, 155.6, 167.2, 198.2.
Elemental analysis : Calculated for C19H18N2O2: C, 74.49 %; H, 5.92 %; N, 9.14 %; Found: C, 74.52 %; H, 5.85 %; N, 9.22 %;

(4Z)-1,3-dibenzyl-4-oxopropylidene)-1,3,4,5-tetrahdro-2H-1,5-benzodiazepin–2-one, 2b

This compound was obtained in 20% yield;
Melting Point: 145-147 °C
1H-NMR (250 MHz, CDCl3): δ= 2.2 (s,3H,CH3), 2.9(m,3H ,CH-CH2 ), 4.8(HAHB,, 2J=15.9Hz, Molbank 2006 m499 i005), 5,4(s,1H, =CH), 7.1-7.3(m, 4H, HArom), 12.6(s, 1H, NH)
13C-NMR (62.9 MHz, CDCl3): δ= 29.9, 31.8, 47.4, 52.7, 93 122.8, 123.2, 125.6, 126.2, 126.5, 126.6, 127.1, 128.4, 128.6, 129.3, 132.0, 135.0, 136.8, 138.7, 158.5, 167.3, 198.0.
Elemental analysis: Calculated for C26H24N2O2: C, 78.76 %; H, 6.10 %; N, 7.07 %; Found: C, 78.80 %; H, 6.04 %; N, 7.10 %;

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-Benzyl (1,3-Dibenzyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one. Molbank 2006, 2006, M499. https://doi.org/10.3390/M499

AMA Style

Said OMSM, Rachid B, Joly N, Lequart V, Martin P, Massoui M, Essassi EM. (4Z)-1-Benzyl (1,3-Dibenzyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one. Molbank. 2006; 2006(5):M499. https://doi.org/10.3390/M499

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-Benzyl (1,3-Dibenzyl)-4-(2-oxopropylidene)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one" Molbank 2006, no. 5: M499. https://doi.org/10.3390/M499

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