A Trifluoroacetic Acid Catalyzed Domino Reaction as an Approach to Amino Acid Derived 2,3-Dihydro-1H-1,5-benzodiazepines

Saurav Bera; Pancham S. Kandiyal; Ravi S. Ampapathi; Gautam Panda

doi:10.1055/s-0033-1340837

Synlett, Inhaltsverzeichnis

Synlett 2014; 25(07): 939-944
DOI: 10.1055/s-0033-1340837

letter

A Trifluoroacetic Acid Catalyzed Domino Reaction as an Approach to Amino Acid Derived 2,3-Dihydro-1H-1,5-benzodiazepines

Saurav Bera

^aMedicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031, UP, India eMail: gautam.panda@gmail.com eMail: gautam_panda@cdri.res.in

,

Pancham S. Kandiyal

^bSophisticated Analytical Instrumental Facility Division, CSIR-Central Drug Research Institute, Lucknow 226031, UP, India

,

Ravi S. Ampapathi

^bSophisticated Analytical Instrumental Facility Division, CSIR-Central Drug Research Institute, Lucknow 226031, UP, India

,

Gautam Panda*

^aMedicinal and Process Chemistry, CSIR-Central Drug Research Institute, Lucknow 226031, UP, India eMail: gautam.panda@gmail.com eMail: gautam_panda@cdri.res.in

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Abstract

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This paper is dedicated to Prof. M. Periasamy on his 60th birthday.

Abstract

Trifluoroacetic acid catalyzed condensation of aromatic amines with substituted benzaldehydes followed by intramolecular cyclization furnishes a highly effective synthesis of amino acid derived 2,3-dihydro-1H-1,5-benzodiazepines. The strategy provides an efficient access to a library of benzodiazepines that can be explored for potential pharmaceutical or biological activities.

Key words

amino acids - heterocycles - benzodiazepine - domino reaction - intramolecular cyclization

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Referenzen

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27 General Experimental Procedure for the Synthesis of 12a–l To a stirred solution of compounds 8a,b (1 equiv) in anhydrous CH₂Cl₂ (10 mL) TFA (2 equiv) was added at 0 °C. The resulting solution was then warmed to r.t. and stirred for 20 min. After this time, the requisite benzaldehyde 10a–l (1.0 equiv) was added slowly, and then the reaction was allowed to stir at r.t. for 10 min. The reaction was quenched by slow addition of a NaHCO₃ solution, and the aqueous layer was extracted with CH₂Cl₂ (2 × 50 mL). Removal of solvent under vacuum and column chromatography of the crude product on silica gel with EtOAc–hexane to furnish compounds 12a–l as colorless oils with. (E)-4-Isopropyl-1-(4-nitrobenzyl)-2,3-dihydro-1H-1,5-benzodiazepine (12g) This product was isolated as a colourless oil; yield 92%. R_f = 0.51 (hexane–EtOAc = 8:2). IR (neat): 3350, 2979, 1633, 1442, 1356, 1149, 674 cm^–1. ¹H NMR (300 MHz, CDCl₃): δ = 8.04 (d, 2 H, J = 8.5 Hz), 7.40 (d, 2 H, J = 8.5 Hz), 7.05–6.84 (m, 4 H), 4.20 (s, 2 H), 3.34 (t, 2 H, J = 6.7 Hz), 2.74–2.65 (m, 1 H), 2.24 (t, 2 H, J = 6.7 Hz), 1.17 (d, 6 H, J = 3.9 Hz) ppm. ¹³C NMR (75 MHz, CDCl₃): δ = 180.2, 147.0, 146.5, 144.1, 139.9, 128.6, 125.2, 125.1, 123.5, 123.2, 119.3, 62.2, 56.3, 38.9, 29.6, 19.8 ppm. ESI-MS: m/z = 324 [M + H]⁺. Anal. Calcd for C₁₉H₂₁N₃O₂: C, 70.57; H, 6.55; N, 12.99. Found: C, 70.65; H, 6.59; N, 12.92.
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