An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium-catalyzed multi-component domino reaction

Dipak Prajapati and Mukut Gohain
Beilstein J. Org. Chem. 2006, 2, No. 11. https://doi.org/10.1186/1860-5397-2-11

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An efficient synthesis of novel pyrano[2,3-d]- and furopyrano[2,3-d]pyrimidines via indium-catalyzed multi-component domino reaction
Dipak Prajapati and Mukut Gohain
Beilstein J. Org. Chem. 2006, 2, No. 11. https://doi.org/10.1186/1860-5397-2-11

How to Cite

Prajapati, D.; Gohain, M. Beilstein J. Org. Chem. 2006, 2, No. 11. doi:10.1186/1860-5397-2-11

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  • Clarke, P. A.; Zaytzev, A. V.; Whitwood, A. C. Pot, atom and step economic (PASE) synthesis of highly functionalized piperidines: a five-component condensation. Tetrahedron Letters 2007, 48, 5209–5212. doi:10.1016/j.tetlet.2007.05.141
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