ugi

=Imine and Ugi synthesis=

The library of [|218 potential enoyl reductase inhibitors] provided by [|Find-A-Drug] consists of diketopiperazine derivatives. The four-component [|Ugi reaction followed by a cyclization] should prove to be a convenient and general approach to making these compounds. Many of these reactions require DOPAL as the aldehyde component. Before attempting the Ugi reaction with DOPAL, we are practicing with other commercially available aldehydes. In the more recent experiments, detailed analysis of the progress of the reactions using NMR with JSpecView permits the determination of the rate constants of imine formation.

More on the Ugi reaction from our Reference page.


 * Experiments in progress or with pending issues are marked by** *

Imine Analysis

__Attempts with DOPAL:__ EXP023 **- Khalid**

__Our most recent attempts__ Exp110 Reaction of the Ugi product 108C with 50% TFA in CDCl3 (prolonged exposure) - **Khalid** / **Jessica** Exp109 Ugi synthesis using 5-(Trifluoromethyl)-2-furylmethylamine, benzaldehyde, benzylisocyanide and boc-glycine - **Khalid** Exp108 Ugi synthesis using furfurylamine, benzaldehyde, benzylisocyanide and boc-glycine - **Khalid** Exp107 Tert-butylation of furfurylamine with t-butanol and Amberlyst 15(H) in CDCl3 at room temperature **- Khalid** Exp105 FriedelCrafts tert-butylation of N-(2-furylmethyl)acetamide**-Khalid** Exp104 Ugi synthesis using furfurylamine, veratraldehyde, tert-butylisocyanide and boc-glycine - **Khalid** Exp103 Synthesis of the acetamide of furfurylamine -**Khalid** Exp102 FriedelCrafts tert-butylation of N-(2-furylmethyl)acetamide**-Khalid** Exp101 Reaction of the Ugi product 99C with 50% TFA in CDCl3 (prolonged exposure) - **Khalid** Exp100 Ugi synthesis using tert-butylamine, benzaldehyde, tert-butylisocyanide and boc-glycine - **Khalid** Exp099 Ugi synthesis using furfurylamine, benzaldehyde, tert-butylisocyanide and boc-glycine - **Khalid** Exp098 Reaction of the Ugi product 64C with 50% TFA in CDCl3 (prolonged exposure) **- Khalid** Exp097 Reaction of the Ugi product 86B with 50% TFA in CDCl3 (prolonged exposure) - **Khalid** Exp096 Ugi synthesis using furfurylamine, veratraldehyde, tert-butylisocyanide and boc-glycine - **Khalid** Exp095 Ugi synthesis using furfurylamine, veratraldehyde, tert-butylisocyanide and boc-glycine - **Khalid** Exp094 3,4-Dihydroxybenzaldehyde, 5-methylfurfurylamine, Boc-Glycine, t-Butyl isocyanide (CHCl3 for imine, MeOH for rxn) - **Sean** Exp093 Ugi synthesis using aniline, benzophenone, tert-butylisocyanide and boc-glycine - **Khalid** Exp092 Test for the stability of the furan ring of amide of BocGlycine and 5MFA in 50% TFA - **Khalid** Exp091 Reaction of the Ugi product 62E with 50% TFA in CDCl3.**Khalid** Exp089 Ugi synthesis using tert-butylamine, benzaldehyde, tert-butylisocyanide and boc-glycine - **Khalid** Exp088 Synthesis of an amide of Boc Glycine and 5-methylfurfurylamine in methanol-d4- **Khalid** *Exp087 Synthesis of the Boc-deprotected amine of the Ugi product 86C**- Khalid** Exp086 Benzaldehyde, 5-methylfurfurylamine, tert-butylisocyanide, Boc-glycine - **Khalid** Exp085Crotonaldehyde, Methylfurfurylamine in CDCl3 - **jgiammarco** Exp084Piperonal, Aniline, Boc-Gly-OH, Tertbutyalisocyanide in CDCl3- **jgiammarco** Exp083Crotonaldehyde, Tertbutyalamine, Boc-Gly-OH, Tertbutylisocyanide in CDCl3- **jgiammarco** Exp082 Synthesis of the Boc-deprotected amine of the Ugi product(64C-2) - **Khalid** Exp081 Test for the stability of the furan ring of N-[(5-methyl-2-furyl)methyl]acetamide in 10% TFA - **Khalid** Exp080 Piperonal, tertbutylamine, Boc-Gly-OH, tertbutylisocyanide (CDCl3) -**jgiammarco** Exp078 Synthesis of the acetamide of 5-methyl furfurylamine -**Khalid** Exp077 Piperonal, tertbutylamine, Boc-Gly-OH(CDCl3) -**jgiammarco** Exp076 Piperonal, tertbutylamine, Boc-Gly-OH (MeOH) -**jgiammarco** Exp073 Test for the stability of the furan ring of 5-Methylfurfurylamine in TFA - **Khalid** Exp070 Ugi Product (diamide) Cycliztion using 50% TFA in CDCl3 - **Khalid** *Exp069 Piperonal, tertbutylamine, Boc-Gly-OH, tertbutyl isocyanide in MeOH-d4 - **jgiammarco** Exp068 Reaction of Boc-Glycine with 10%TFA in CDCl3 - **Khalid** Exp067 Ugi Product (diamide) Cycliztion using 10% TFA in CDCl3 - **Khalid** Exp066 Piperonal, tertbutylamine, Boc-Gly-OH, tertbutyl isocyanide in MeOH-d4 - **jgiammarco** *Exp065 Ugi Product (diamide) Cycliztion using 10% TFA in CDCl3 - **Alicia** *Exp064 [Veratraldehyde, 5-Methyl furfurylamine], Benzyl Isocyanide, Boc-Gly-OH in MeOH - **Khalid** *Exp063 3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine, Boc-Gly-OH, benzyl isocyanide - **Sean** *Exp062 Piperonal, 5-methylfurfurylamine, Boc-Gly-OH, tertbutyl isocyanide in MeOH - **Alicia** *Exp061 3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine, Boc-Gly-OH, benzyl isocyanide - **Sean** *Exp060 [Veratraldehyde, 5-Methyl furfurylamine], Benzyl Isocyanide, Boc-Gly-OH in MeOH- **Khalid** *Exp059 Piperonal, 5-methylfurfurylamine, Boc-Gly-OH, tertbutyl isocyanide in MeOH - **Alicia** *Exp058 Piperonal, tertbutylamine, Boc-Gly-OH, tertbutyl isocyanide in MeOH-d4 - **jgiammarco** Exp057 (3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine in MeOH-d4) - **Sean** Exp056 Boc-Met-OH and 5-Methyl furfurylamine in MeOH-d4 - **Khalid** Exp055 Boc-Gly-OH and 5-Methyl furfurylamine in MeOH-d4 - **Khalid** Exp054 [Veratraldehyde, 5-Methyl furfurylamine], Benzyl Isocyanide and final addition of Boc-Gly-OH in MeOH-d4 - **Khalid** Exp053 Boc-Gly-OH and //tert//-butyl isocyanide in MeOH-d4 - **Khalid** *Exp052 Piperonal, 5-methylfurfurylamine, BocGly-OH, //tert//-butyl isocyanide in MeOH - **Alicia** Exp051 Piperonal and //tert-//butylamine, Boc-Gly-OH and dehydration with MgSO4 in MeOH-d4 **- jgiammarco** Exp050 Boc-Gly-OH and Benzyl isocyanide in MeOH-d4 - **Khalid** Exp049 Boc-Gly-OH and 2-morpholinoethyl isocyanide in MeOH-d4 - **Khalid** *Exp048 (piperonal, tertbutylamine, Boc-Gly-OH, 2-morpholino ethylisocyanide in MeOH-d4) - **jgiammarco** Exp047 (3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine in MeOH-d4) - **Sean** Exp046 (3,4-dimethoxybenzaldehyde, 5-methylfurfurylamine, BocGly, 2-morpholinoethylisocyanide in MeOH-d4) **- Khalid** *Exp045 (3,4-dimethoxybenzaldehyde, 5-methylfurfurylamine, BocGly, 2-morpholinoethylisocyanide in CDCl3) **- Khalid** Exp044 Formation of the imine of Phenyl acetaldehyde and //tert-//butylamine in CDCl3- **Khalid** Exp043 Formation of the imine of Piperonal and 5-Methyl furfurylamine in MeOH-d4 - **Alicia** Exp042 Formation of the imine of Phenyl acetaldehyde and //tert-//butylamine in CDCl3- **Khalid / Lin** Exp041 Formation of the imine of Piperonal and 5-Methyl furfurylamine in MeOH-d4- **Alicia** Exp040 Formation of the imine of Piperonal and 5-Methyl furfurylamine in CDCl3- **Alicia** Exp038 (Phenylacetaldehyde, 5-methylfurfurylamine, BocGly, 2-morpholinoethylisocyanide in CDCl3 ) - **Alicia** Exp034 (Phenylacetaldehyde, 5-methylfurfurylamine, BocGly, 2-morpholinoethylisocyanide in CDCl3) - **Alicia** Exp032 (Imine mix from Exp036, Boc-Met-OH, 2-morpholinoethylisocyanide in MeOH ) - **Khalid** Exp031 (Phenylacetaldehyde after distillation, -methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH ) **- Jgiammarco** Exp030 (Piperonal, tertbutylamine, Boc-Gly-OH, 2-morpholino ethylisocyanide in MeOH) **- Khalid** Exp029 (Piperonal, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH then CDCl3) - **Alicia** Exp028 (Formaldehyde, tertbutylamine, Boc-Gly-OH, 2-morpholino ethylisocyanide in 1M LiCl/Water) - **Khalid** Exp027 (Formaldehyde, tertbutylamine, Boc-Gly-OH, 2-morpholino ethylisocyanide in Methanol) **-** **Khalid** Exp026 (Piperonal, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH ) **Lin** EXP022 (3,4-dimethoxybenzaldehyde, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH ) **Khalid** EXP021 (3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH ) **jgiammarco** EXP020 (3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH ) **jgiammarco** EXP019 (Piperonal, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH) - **Lin** EXP018 (3,4-dihydroxybenzaldehyde, 5-methylfurfurylamine, BocGly-OH, benzylisocyanide in MeOH) **jgiammarco** EXP017 (Piperonal, 5-methylfurfurylamine, BocMet-OH, benzylisocyanide in MeOH) - **Lin** EXP014 (Phenylacetaldehyde, 5-methylfurfurylamine, BocMet-OH, benzylisocyanide in MeOH) **- Khalid** [|EXP006] (Phenylacetaldehyde, 5-methylfurfurylamine, Boc-Met-OH, benzylisocyanide in MeOH) **- Khalid** [|EXP003] (Phehylacetaldehyde, 5-methylfurfurylamine, Boc-Met-OH, benzylisocyanide in MeOH) - **Brett/Alicia/jgiammarco**

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