Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 2, Pages 1925-1937Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02152
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Funding
- Council of Scientific and Industrial Research (CSIR) Project [02(0376)/19/EMR-II]
- University Grants Commission (UGC)-Mid Career Award New Delhi [F-19-230/20189(BSR)]
- University Grants Commission (UGC) New Delhi
- Council of Scientific and Industrial Research (CSIR) New Delhi
- Department of Science and Technology Funds for the Improvement of Science and Technology (DST-FIST) New Delhi
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The one-pot synthesis of 3,4-benzo[c]-beta-carbolines and related compounds was successfully achieved through intramolecular Heck coupling reaction, with the ability to control product formation by employing specific protecting groups on different parts of the molecule.
One-pot synthesis of 3,4-benzo[c]-beta-carbolines was achieved from 2-aryl(tosylamino)methyl-3-bromoindoles via 10 mol % Pd(OAc)(2)/PPh3-mediated intramolecular Heck coupling using K2CO3 as a base in DMF at 110 degrees C with concomitant aromatization through an elimination of tosylsulfinic acid. Under identical conditions, the isomeric 3-aryl(tosylamino)methyl-2-bromoindoles upon intramolecular Heck reaction furnished benzo[4,5]isothiazolo[2,3-a]indole 5,5-dioxides instead of the expected gamma-carbolines. However, synthesis of the expected gamma-carboline framework, 3-tosyl-6,9-dihydro-1,2-benzo[a]-gamma-carbolines, could be achieved from 3-aryl(tosylamino)methyl-2-bromoindoles containing a mesitylene sulfonyl unit as a protecting group on the indole nitrogen.
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