Abstract
(E)-3-(2-Methyl-1H-indol-3-yl)-1-(4-methylphenyl)propenone has been prepared, and its crystal structure (C19H17NO, Mr = 275.34) has been determined by single-crystal X-ray diffraction analysis. The title compound crystallized in the triclinic system with space group P1 and unit cell parameters: a = 9.4014 (5) A, b = 9.8347 (4) A, c = 10.0318 (5) A, α = 62.821 (3)°, β = 85.539 (3)°, γ = 65.262 (3)° and Z = 2. The final reliability index is 0.053 for the 2807 observed reflections. The title compound is linked through N–H···O hydrogen bonds.
Highlights
The indole scaffold is a prominent and privileged structural motif found in numerous natural products and various synthetic compounds
Prompted by the above we recently reported an environment friendly KHSO4-assisted Michael addition–elimination reactions of indole with 3-dimethylamino-1-phenylprop-2-en-1-ones in water that leads to the formation of 3-indolylchalcones
Intermolecular hydrogen bonding is seen between N–H of indole ring and carbonyl O (Figure 2).The D—H···A angle is 140.7° while H···A distance is 2.007 Å (Table 2)
Summary
The indole scaffold is a prominent and privileged structural motif found in numerous natural products and various synthetic compounds. Libraries based on the indole scaffold have been developed to address the need for novel drugs with increased potency[3,4]. In this study we envisaged cyclisation of the indolylchalcones to give carbazole under the reaction conditions but no trace of this product was formed. Confronted by this difficulty, we decided to study the details of the structure of 3 which held it back from cyclisation to give the envisaged carbazole 4 shown in Scheme 1
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