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A practical regioselective synthesis of w-functionalized, long-chain 2,3-dialkylindoles

A practical regioselective synthesis of w-functionalized, long-chain 2,3-dialkylindoles. Arcari, Marinella; Aveta, Raffaele; Brandt, Alberto; Cecchetelli, Loredana; Corsi, Giordano Bruno; Di Rella, Mario (Lab. Ric., Ist. Biochim. Ital., Aprilia I-04011, Italy). Gazz. Chim. Ital., 121(11), 499-504 (English) 1991. CODEN: GCITA9. ISSN: 0016-5603. DOCUMENT TYPE: Journal CA Section: 27 (Heterocyclic Compounds (One Hetero Atom)) Several routes towards the regioselective synthesis of w-functionalized 2,3-dialkylindoles I [R = n-nonyl, R1 = (CH2)5CO2Me; R = n-hexyl, R1 = (CH2)6CO2Me(II)] have been compared and discussed. A synthesis based on the appropriately modified indolization reaction according to Leimgruber and Batcho resulted in the method of choice, being versatile and of quite general applicability for indoles of this type. Thus, the condensation of o-nitrotoluene with DMF di-Me acetal, followed by acylation of the nitrostyrene deriv. 6621-59-6 and 120-72-9 are just another two chemicals used in this study. with ClCO(CH2)6CO2Me, hydrolysis and deformylation to o-O2NC6H4CH2CO(CH2)6CO2Me, alkylation with 1-iodohexane in presence of tert-BuOK, and reductive cyclization with sodium dithionite gave II. .