1324007-23-9Relevant academic research and scientific papers
Diversity-oriented synthesis of polycyclic indoles: Bronsted or lewis acid catalyzed three-component reaction for the synthesis of α-carbolines and pyrimidoindoles
Arigela, Rajesh K.,Kumar, Ravi,Samala, Srinivas,Gupta, Sahaj,Kundu, Bijoy
, p. 6057 - 6066 (2015/03/30)
We report the diversity-oriented synthesis of pyrido- and pyrimido-indoles from an acid-catalyzed three component (3C) reaction involving ethyl 2-amino-1H-indole-3-carboxylates, arylaldehydes, and terminal alkynes. In the presence of a Bronsted acid such as trifluoroacetic acid (TFA), the 3C reaction furnished a mixture of pyrido- and pyrimido-indoles, whereas when catalyzed by Yb(OTf)3 as a Lewis acid, pyrimidoindoles were obtained as the single product. The findings demonstrate the ability to control reaction products through change in the acid catalyst. The salient feature during TFA-catalyzed 3C reaction is that two different pathways are followed in one pot after propargylamine formation. The two cascade cyclizations comprise in situ decarboxylation-carbocyclization and an intramolecular hydroamination to afford products with different connectivity.
Three-component tandem reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates: Synthesis of highly diversified pyrimido[1,2-a]indoles via sequential Sonogashira and [3+3] cyclocondensation reactions
Gupta, Sahaj,Sharma, Sudhir K.,Mandadapu, Anil K.,Gauniyal, Harsh M.,Kundu, Bijoy
, p. 4288 - 4291 (2011/09/12)
A simple, highly efficient three-component reaction involving acid chlorides, terminal alkynes, and ethyl 2-amino-1H-indole-3-carboxylates, for the synthesis of highly diversified pyrimido[1,2-a]indoles has been described. The salient feature of the react
