caa a22 4500 445875895 CHVBK 20180317145527.0 cr unu---uuuuu 170323e20111201xx s 000 0 eng 10.1007/s10593-011-0878-x doi (NATIONALLICENCE)springer-10.1007/s10593-011-0878-x Synthesis of 1-(oxiran-2-ylmethyl)-1 H -indole-3-carbaldehyde and its reaction with active methylene compounds [Elektronische Daten] [K. Suzdalev, S. Den'kina] Treatment of indole-3-carbaldehyde with epichlorohydrin gave 1-(oxiran-2-ylmethyl)-1H-indole-3-carb-aldehyde, reaction of which with 1,3-dimethylbarbituric acid or malononitrile gave crotonic condensation products with retention of the oxirane ring. The structure of the reaction products with aroylglycines depends on the conditions. In acetic anhydride a simultaneous formation of an oxazolone ring and bisacylation of the oxirane fragment occurs; the use of ethyl chloroformate in the presence of triethylamine allows to carry out only the heterocyclization process. When treated with the cyclic amines (N-methylpiperazine or morpholine) opening of the oxazolone ring in the products occurs with formation of the corresponding amides. Springer Science+Business Media, Inc., 2011 amide nationallicence indolylmethyleneoxazolone nationallicence 1-(oxiran-2-ylmethyl)-1H-indole-3-carbaldehyde nationallicence crotonic condensation nationallicence oxazolone ring opening nationallicence Suzdalev K. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090, Rostov-on Don, Russia aut Den'kina S. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090, Rostov-on Don, Russia aut Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/9(2011-12-01), 1085-1090 0009-3122 47:9<1085 2011 47 10593 https://doi.org/10.1007/s10593-011-0878-x text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/s10593-011-0878-x text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Suzdalev K. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090, Rostov-on Don, Russia aut NATIONALLICENCE 700 1- Den'kina S. Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka Ave., 344090, Rostov-on Don, Russia aut NATIONALLICENCE 773 0- Chemistry of Heterocyclic Compounds Springer US; http://www.springer-ny.com 47/9(2011-12-01), 1085-1090 0009-3122 47:9<1085 2011 47 10593 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer