@article {43879, title = {Pd-catalyzed regioselective mono-arylation: quinazolinone as the inherent directing group for C(sp(2))-H activation}, journal = {Journal of Organic Chemistry}, volume = {82}, year = {2017}, month = {JUN}, pages = {6366-6372}, type = {Article}, chapter = {6366-6372}, abstract = {

The Pd-catalyzed quinazolinone-directed regioselective monoarylation of aromatic rings by C-H bond activation is developed. A broad substrate scope is demonstrated for both quinazolinone as well as diary-liodonium triflates. The use of a base was found to be crucial for this transformation, unlike for the known nitrogen-directed arylations. All of the novel quinazolinones of biological interest were synthesized by using the operationally simple Pd(II)-catalyzed arylation reaction.

}, keywords = {Aromatic rings, catalysis, Chemical activation, Chemical reactions, Palladium compounds, Regioselectivity}, issn = {0022-3263}, doi = {10.1021/acs.joc.7b00948}, author = {Garad, Dnyaneshwar N. and Viveki, Amol B. and Mhaske, Santosh B.} } @article {45438, title = {Ruthenium-catalyzed regioselective alkenylation/tandem hydroamidative cyclization of unmasked quinazolinones using terminal alkynes}, journal = {Journal of Organic Chemistry}, volume = {83}, year = {2018}, month = {AUG}, pages = {8906-8913}, type = {Article}, abstract = {

Ruthenium-catalyzed amide directed C-sp2-H activation of the quinazolinone scaffold has been demonstrated, leading to the selective mono- or dialkenylation in moderate to good yields to achieve medicinally important stilbene containing quinazolinones. The terminal allcyne is utilized as a coupling partner, which resulted in the selective trans-alkene formation. Electron-deficient phenylacetylenes facilitate alkenylation followed by tandem hydroamidation of the newly generated trans double bond to provide novel quinazolinone alkaloids related to the Luotonine class of natural products.

}, doi = {10.1021/acs.joc.8b01143}, author = {Viveki, Amol B. and Mhaske, Santosh B.} } @article {46966, title = {Para-selective copper-catalyzed C(sp(2))-H amidation/dimerization of anilides via a radical pathway}, journal = {Chemical Communications}, volume = {56}, year = {2020}, month = {FEB }, pages = {1565-1568}, type = {Article}, abstract = {

Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp(2))-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.

}, issn = {1359-7345}, doi = {10.1039/c9cc09824k}, author = {Viveki, Amol B. and Garad, Dnyaneshwar N. and Gonnade, Rajesh G. and Mhaske, Santosh B.} } @article {47651, title = {Annulation of enals with carbamoylpropiolates via NHC-catalyzed enolate pathway: access to functionalized maleimides/iso-maleimides and synthesis of aspergillus FH-X-213}, journal = {Journal of Organic Chemistry}, volume = {86}, year = {2021}, month = {JUL }, pages = {9466-9477}, type = {Article}, abstract = {Herein we report the N-heterocyclic carbene (NHC)-catalyzed [3 + 2] annulation of alpha,beta-unsaturated aldehydes with carbamoylpropiolates via an unusual enolate pathway leading to the construction of highly functionalized maleimides or isomaleimides. The electronic effect imposed by the alkyl/aryl group present on the amide nitrogen of carbamoylpropiolates plays a crucial role in the selective formation of these important five-membered heterocyclic building blocks. The developed protocol is mild and tolerates a wide range of substituents on both substrates. The application of this protocol in the synthesis of the antibacterial natural product Aspergillus FH-X-213 has also been demonstrated.}, issn = {0022-3263}, doi = {10.1021/acs.joc.1c00782}, author = {Viveki, Amol B. and Pol, Mahesh D. and Halder, Priyanka and Sonavane, Sameer R. and Mhaske, Santosh B.} }