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Issue 16, 2012
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One pot synthesis of maleimide and hydantoin by Fe(CO)5 catalyzed [2 + 2 + 1] co-cyclization of acetylene, isocyanate and CO

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Abstract

In the presence of a catalytic amount of Fe(CO)5, terminal acetylenes, isocyanates and CO undergo [2 + 2 + 1] cyclization to form substituted maleimides and hydantoins; when internal alkynes are used, exclusive maleimide formation is observed. While the maleimides can be obtained as the major products, in up to 90% yield, when the reaction is carried out in CO atmosphere, in absence of CO, the hydantoins are formed in up to 87% yield. Formation of maleimides has been shown to occur via the formation of a ferrole intermediate, whereas the hydantoins are proposed to form through successive insertion of isocyanate into the iron–acetylide bond. All compounds were characterized by spectroscopic methods and molecular structures of some compounds were established by single crystal X-ray diffraction method.

Graphical abstract: One pot synthesis of maleimide and hydantoin by Fe(CO)5 catalyzed [2 + 2 + 1] co-cyclization of acetylene, isocyanate and CO

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Publication details

The article was received on 14 Oct 2011, accepted on 08 Feb 2012 and first published on 07 Mar 2012


Article type: Paper
DOI: 10.1039/C2DT11942K
Dalton Trans., 2012,41, 5045-5054

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    One pot synthesis of maleimide and hydantoin by Fe(CO)5 catalyzed [2 + 2 + 1] co-cyclization of acetylene, isocyanate and CO

    P. Mathur, R. K. Joshi, D. K. Rai, B. Jha and S. M. Mobin, Dalton Trans., 2012, 41, 5045
    DOI: 10.1039/C2DT11942K

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