Conjugate Addition of Indoles and Pyrroles to Dihydronitronaphthalenes in Water: Synthesis of 3,4-Fused Tetrahydro-β-carbolines (pages 772–780)
Rajesh Malhotra, Rajib Ghosh, Tushar K. Dey, Sagar Chakrabarti, Amit Ghosh, Swarup Dutta, Sonika Asijaa, Subho Roy, Shantanu Dutta, Sourav Basu and Saumen Hajra
Article first published online: 14 DEC 2012 | DOI: 10.1002/ejoc.201201288
A catalyst-free conjugate addition of indoles and pyrroles to 1,2-dihydro-3-nitronaphthalenes in water provides 1-heteroaryl-2-nitrotetralins with moderate to good diastereoselectivity and yields. The utility of the method was demonstrated by Suzuki coupling of the bromo functionality of the adducts and the synthesis of 3,4-fused tetrahydro-β-carbolines, a new class of compounds.