127744-44-9Relevant articles and documents
First isolation of both indolylcarbinols and diindolylalkanes from microwave-assisted acid (clay)-catalysed reaction of indoles with diethyl ketomalonate
Chakrabarty, Manas,Karmakar, Sulakshana,Harigaya, Yoshihiro
, p. 37 - 48 (2007/10/03)
Indoles (1a-f) react with diethyl ketomalonate on montmorillonite K10 clay under microwave irradiation to furnish expeditiously (1-4 min) the corresponding indol-3′-ylcarbinols (2a-f; 20-45%) and the respective diindolylalkanes (3a-f; 5-35%), which constitute the first direct evidence for the intermediacy of indolylcarbinols in the formation of diindolylalkanes from the acid-catalysed reaction of indoles with aldehydes and ketones.
FIRST REACTIONS OF VINYLINDOLES WITH DIETHYL MESOXALATE, NITROSOBENZENE, AND CHLOROSULFONYL ISOCYANATE: NEW FUNCTIONALIZED AND ANNELLATED INDOLES
Pindur, Ulf,Kim, Myung-Hwa
, p. 6427 - 6438 (2007/10/02)
Diethyl mesoxalate reacts with 2- and 3-vinylindoles via electrophilic substitution to give new, functionalized and annellated indoles in high regioselectivities.Regio-controlled dimerization processes occur in the reactions of the vinylindoles 5a and 8a.Nitrosobenzene reacts with 2- and 3-vinylindoles in a multi-stage sequence including regiospecific tandem hetero-Diels-Alder reactions to give the new, 2,3-difunctionalized indoles 11 and 12 which are conformationally stabilized by proton chelation.The heterocumulenechlorosulfonyl isocyanate reacts as a simple electrophile (like diethyl mesoxalate) with 2-vinylindole 5b to give the indole-3-carboxamide 14.In addition, analogous reactions of N-methylindole were also studied and, in most cases, gave comparable reactivity patterns.
