Synthesis of polyfunctionalized pyrroles bearing C-2 α-azido side-chains and displacement of the α-azido group by various nucleophiles

Synthesis of Polysubstituted 5,6-Dihydropyrrolo[3,4-b]pyrrol-4(1H)-ones from 2-[Aryl(azido)methyl]-1H-pyrrole-3-carboxylates via a Concise Three-Step Sequence

“…In our laboratory, we have developed several novel reactions that provide easy access to useful functionalized N-containing heterocycles of chemical and biological interest. [7][8][9] As a continuation of our research investigating multicomponent reaction using α,γ-diazido-α,β-unsaturated esters, we herein report a novel for the construction of 5,6-dihydropyrrolo [3,4-b]pyrrol-4(1H)-ones.…”

Recent Advances for the Synthesis of N‐Unsubstituted Pyrroles

“…Kishii N. et al 69 presented a new approach for the preparation of polyfunctionalized pyrroles. The first stage is based on reaction of diazides 210 and 1,3-dicarbonyl compounds yielding tetrasubstituted pyrroles 211 bearing α-azido group.…”

Synthesis of Highly Functionalized 4-Amino-2-(trifluoromethyl)-1H-pyrroles

“…bis(butyl)-5-(trifluoromethyl)-1H-pyrrol-3-amine hydrochloride (3a) Light yellow solid; yield: 268 mg, 90%; m. p.: 99 -100 °C.1 H NMR (400 MHz, CDCl3)  = 11.05 (brs, 1H), 7.23 (d, 1H, J = 2.1 Hz),6.70 (d, 1H, J = 2.0 Hz), 3.92 (t, 2H, J = 8.0), 3.18 (t, 2H, J = 8.0), 1.87 -1.79 (m, 2H), 1.78 -1.71 (m, 2H), 1.38 -1.33 (m, 4H), 0.94 (t, 3H, J = 7.4 Hz), 0.89 (t, 3H, J = 7.4 Hz).13 C NMR (100 MHz, CDCl3):  = 121.3 (q, 2 JC-F = 39.3 Hz), 120.6 (q, 1 JC-F = 267.5 Hz), 119.7, 118.3, 105.9 (q,3 JC-F = 3.2 Hz), 52.8, 48.7, 33.2, 27.5, 20.0, 19.9, 13.6, 13.5. GC-MS (EI, 70 eV): m/z (%) = 262 (29) [M + ], 219 (100), 163 (19).…”

“…Pyrrole motifs, which are present in many important natural products and many other derivatives that exhibit biological or pharmacological activity of general interest, have been attracting much attention from synthetic organic chemists over the last decade, [1][2][3][4][5][6][7][8] and have been used as antitumor, anti-inflammatory, antifungal, and antioxidant agents, to name just a few. [9][10][11][12] In addition, the incorporation of a trifluoromethyl group into heterocycles has been of great interest, because this highly electronegative group can affect both physical and chemical properties, in terms of metabolic stability, lipophilicity, binding selectivity, and bioavailability.…”