A Simple Procedure for the Preparation of 6‐Chloro‐3‐acetoxy‐1‐acetylindole.

Abstract

Indole derivatives R 0140A Simple Procedure for the Preparation of 6-Chloro-3-acetoxy-1-acetylindole. -An overall yield of 38% for compound (V) is reported. -(BALBUZANO-DEUS, A.; RODRIGUEZ-DOMINGUEZ, J. C.; FERNANDEZ-VILLALOBO, A.; LOPEZ-LOPEZ, M.; KIRSCH*, G.; Org.

The Ullmann Coupling between 2-Chlorobenzoic Acids and Amino Acids; A Valuable Reaction for Preparing 2-Substituted 1-Acetyl-1H-indol-3-yl Acetates­

“…4 In previous work we reported a simple two-step procedure for the preparation of 3-acetoxy-1-acetyl-6-chloro-1H-indole from 2,4-dichlorobenzoic acid and an unactivated amino acid in good yield. 5 Encouraged by this result, we decided to carry out the preparation of other substituted 3acetoxy-1-acetyl-1H-indoles starting from the corresponding 2-chlorobenzoic acids. 6 These papers made us think about the possibility of using the same procedure to prepare 2-substituted 3-acetoxy-1-acetyl-1H-indoles 6 from 2-chlorobenzoic acids 1 and 2-substituted amino acids 2 or 5-aminopentanoic acid (3).…”

“…These compounds were prepared according to a previously reported procedure. 5,6 Mass spectra were not possible to obtain due to rapid thermal decomposition once they were injected into the equipment.…”

An improved synthesis of 1‐acetyl‐1H‐indol‐3‐yl acetates

“…For this procedure long reaction time is required for the aminoalkylation step and poor yields are obtained [5], even in the case of 1-acetyl-1H-indol-3-yl acetate [6]. In a previous work we described an improved two steps procedure for obtaining 3b starting from 2,4-dichlorobenzoic acid [7]. Encouraged by this result, we decided to carry out the preparation of other substituted 1-acetyl-1H-indol-3-yl acetate derivatives starting from the corresponding 2-chloro benzoic acids.…”

Jones–Schmid Indole Synthesis

“…Some additional examples of this N,O-diacetylindoxyl preparation are shown in Table 3 [32][33][34][35][36][37][38]. The chemistry by Funk and Huntley in Entry 4 was a key feature in their synthesis of the dragmacidin E core system [36].…”