77435-12-2Relevant academic research and scientific papers
Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles
Nemoto, Koji,Tanaka, Shinya,Konno, Megumi,Onozawa, Satoru,Chiba, Masafumi,Tanaka, Yuuki,Sasaki, Yosuke,Okubo, Ryo,Hattori, Tetsutaro
, p. 734 - 745 (2016)
Various 1-methyl-, 1-triisopropylsilyl-, and 1-benzylindoles are carboxylated under CO2 pressure (3.0 MPa) with the aid of 1.0 molar equiv of Me2AlCl to give 1-substituted indole-3-carboxylic acids in good to excellent yields. Mechanistic studies suggest that the intermediate, an indol-3-ylaluminum ate complex, was reversibly formed by electrophilic addition of Me2AlCl to the substrate followed by deprotonation of the resulting adduct. This method is successfully extended to alkoxycarbonylation with ethyl chloroformate and carbamoylation with naphthalen-1-yl isocyanate, which afford ethyl indole-3-carboxylates and N-naphthalen-1-ylindole-3-carboxamides, respectively.
A convenient and general method for the synthesis of indole-2,3- dicarboxylates and 2-arylindole-3-carboxylates
Sayyed, Iliyas Ali,Alex, Karolin,Tillack, Annegret,Schwarz, Nicolle,Michalik, Dirk,Beller, Matthias
, p. 4525 - 4528 (2008/02/12)
A transition-metal-free, simple and efficient one-pot method for the synthesis of indole-2,3-dicarboxylates and 2-aryl-indole-3-carboxylates is described. The corresponding products are obtained by a domino hydroamination/Fischer indole cyclization in goo
Fischer Indole Synthesis of 3-Acyl and 3-Alkoxy-carbonylindoles
Mills, Keith,Khawaja, Ibtisam K. Al,Al-Saleh, Fowzia,Joule, John A.
, p. 636 - 641 (2007/10/02)
N-Benzyl-N-phenylhydrazine derivatives of 1,3-diketones and 1,3-ketoesters undergo normal Fischer cyclisations to indoles, but no method could be found for the subsequent removal of the N-protecting group.No method could be found for the indolisation of N-aroyl-N-phenylhydrazine derivatives of dimedone with retention of the N-protecting group, though heating in tetralin did effect the electrocyclic step of the Fischer sequence and the formation of a carbon-carbon bond.
