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Synthesis 2021; 53(06): 1127-1136
DOI: 10.1055/s-0040-1707312
paper

Synthesis of Fused Pyrimido[1,6-a]indolones via Rhodium(III)-Catalyzed Cascade Annulations

Chada Raji Reddy  ∗
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India   Email: rajireddy@iict.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Srinivas Bodasu
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India   Email: rajireddy@iict.res.in
,
Kathe Mallesh
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India   Email: rajireddy@iict.res.in
b   Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, India
,
Y. Lakshmi Prapurna
a   Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology (CSIR-IICT), Hyderabad 500007, India   Email: rajireddy@iict.res.in
› Author AffiliationsC.R.R. thanks the Science and Engineering Research Board (SERB), New Delhi, for funding the project (EMR/2016/006253). Y.L.P. thanks Department of Science and Technology (DST) for a financial grant under Women Scientists Scheme-A [WOS-A, Grant No. SR/WOS-A/CS-1034/2014 (G)]. S.B. and K.M. thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for research fellowships.
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This work is dedicated to Dr. J. S. Yadav on the occasion of his 70th birthday for his contributions to organic synthesis

Abstract

A novel method for the synthesis of fused pyrimido[1,6-a]-indolone derivatives by annulation of 2-alkynylaryl aldehydes/2-alkynyl­arylidene ketones with N-(pivaloyloxy)-1H-indole-1-carboxamide catalyzed by rhodium has been accomplished. The reaction proceeds through C–H activation based annulation with alkyne moiety followed by addition of nitrogen on to aldehyde/activated alkene to give the products in moderate to good yields. Highly fluorescent dipyrrinone analogues could be synthesized from the derived products.

Key words

N-(pivaloyloxy)-1H-indole-1-carboxamide - C–H activation - aza-Michael addition - cascade annulation - pyrimido[1,6-a]indolone

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707312. Copies of 1H and 13C NMR spectra for all new compounds are provided.
  • Supporting Information


Publication History

Received: 07 August 2020

Accepted after revision: 04 September 2020

Article published online:
12 October 2020

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