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Conjugate Addition of Indoles and Pyrroles to Dihydronitronaphthalenes in Water: Synthesis of 3,4‐Fused Tetrahydro‐β‐carbolines
Author(s) -
Malhotra Rajesh,
Ghosh Rajib,
Dey Tushar K.,
Chakrabarti Sagar,
Ghosh Amit,
Dutta Swarup,
Asijaa Sonika,
Roy Subho,
Dutta Shantanu,
Basu Sourav,
Hajra Saumen
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201288
Subject(s) - chemistry , conjugate , amine gas treating , combinatorial chemistry , catalysis , nitro , organic chemistry , mathematical analysis , alkyl , mathematics
A catalyst‐free conjugate addition of indoles and pyrroles to 1,2‐dihydro‐3‐nitronaphthalenes in water has been developed. A variety of indoles containing electron‐rich and ‐deficient functional groups including aza‐indoles and pyrroles reacted smoothly with a number of dihydro‐3‐nitronaphthalenes, especially bromo derivatives. For structural elaboration, the bromo functionality (dihydronitronaphthalene unit as well as indolyl unit) of the addition products was utilized for Suzuki coupling reactions and provided moderate to good yields of the desired coupling compounds. The utility of the method was further demonstrated by the synthesis of 3,4‐fused tetrahydro‐β‐carbolines, a new class of compounds, from the addition products through reduction of the nitro group to the amine and subsequent Pictet–Spengler cyclization.