Molecular‐Iodine‐Catalyzed One‐Pot Synthesis of 1,5‐Benzodiazepine Derivatives under Solvent‐Free Conditions.

Abstract

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Solvent-Free Syntheses of 1,5-Benzodiazepines Using HY Zeolite as a Green Solid Acid Catalyst

“…8−11 Over the past several years, considerable studies have been reported for the synthesis of 1,5-benzodiazepines utilizing ytterbium triflate, 12 gallium(III)triflate, 13 erbium(III)triflate, 14 scandium(III)triflate, 15 ytterbium perfluorooctanesulfonate, 16 BF 3 -etherate, 17 p-toulenesulfonic acid, 18 NaBH 4 , 19 MgO/POCl 3 , 20 polyphosphoric acid, 21 CeCl 3 -NaI/SiO 2 , 22 Al 2 O 3 /P 2 O 5 , 23 sulfated zirconia, 24 1,3-n-dibutylimidazolium bromide, 25 SbCl 3 -Al 2 O 3 , 26 iodine, 27 magnesium perchlorate, 28 sodium dodecyl sulfate, 29 Ag 3 PW 12 O 40 , 30 zinc chloride, 31 dodecyl sulfonic acid, 32 piperidine acetic acid, 33 La(NO 3 ) 3 , 34 SmI 2 , 35 sulfamic acid, 36 organic acid, 37 HClO 4 -silica, 38 YbCl 3 , 39 ceric ammonium nitrate, 40 N-bromosuccinimide, 41 acetic acid/MW, 42 (NH 4 )-H 2 PW 12 O 40 , 43 SnCl 2 , 44 K10-montmorillonite, 45 Zn-montmorillonite heterogeneous catalysts 46 borax/phosphorus oxychloride, 47 amberlyst-15, 48 InBr 3 , 49 InCl 3 , 50 NbCl 5 , 51 and RuCl 3 • xH 2 O 52 as catalysts. In addition, a solvent-free procedure has been reported for the synthesis of 1,5-benzodiazepines using iodine, 53 silver nitrate, 54 and HBF 4 -SiO 2…”

Greener and Efficient Synthesis of Benzodiazepines Using Mixed Ferriteunder Solvent Free Condition

“…Benzodiazepines are commonly synthesized by the cyclocondensation of o-phenylenediamine with α,βunsaturated carbonyl compounds(chalcones), αhaloketones, or with ketones [13] using various acidic catalysts which are critical to transformation into suitable product. Different reagents such as boron trifluorideetherate, polyphosphoric acid, sodium borohydride,MgO/POCl3,Yb(OTf)3,Ga(OTf)3,Pb(NO3)2,L -proline,CH3COOH under microwave irradiation, molecular I2, and various greener solvents have also been used for the synthesis of benzodiazepines [14][15][16][17][18][19][20][21][22][23][24]. But literature reports shows that majority of these catalysts have one or more limitations, such as longer reaction time, generation of several biproducts, severe reaction conditions, low yields, and tedious workup.…”

Efficient TCT-catalyzed Synthesis of 1,5-Benzodiazepine Derivatives under Mild Conditions

“…[ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 ]. These reactions also occur with various catalysts under solvent free conditions [ 27 , 28 , 29 , 30 ]. Nevertheless, many of these methods suffer from shortcomings such as long reaction times, harsh reaction conditions, low product yields, occurrence of several side products and difficulties in recovery of the products.…”