1618098-99-9Relevant academic research and scientific papers
A novel tandem Pd-catalyzed intramolecular allylic decarboxylative coupling and “diradical conjugated 1,3-dien-5-yne cycloaromatization”: An unusual ortho-selectivity in the cycloaromatization and the mechanistic implications
Tummanapalli, Satyanarayana,Vangapandu, Dhanunjaya Naidu,Muthuraman, Parthasarathy,Kambampati, Sanjeeva,Shanmugavel, Gnanakalai
supporting information, p. 3125 - 3131 (2017/07/18)
A domino fashioned allylic rearrangement, intramolecular decarboxylative coupling, propargyl-allene rearrangement and diradical 1,3-dien-5-yne cycloaromatization of aryl propiolates of the Baylis-Hillman alcohols in the presence of catalytic Pd(PPh3)4 and DBU leading to the formation 4-benzylnaphthoates has been described. Interestingly, the meta-substituted propiolates (1i–t) provided sterically hindered cyclization products (12–23) via the unusual ortho-selective cycloaromatization; while the meta-alkoxy (1i–m, 1r–t) group provided predominantly the ortho-selective 1,3-dien-5-yne cycloaromatization products, meta-Me group (1?n–q), products formed both via ortho-selective cyclization and para-selective cyclization products in comparable ratio. A novel mechanism involving diradical species has been proposed to explain the unusual ortho-selectivity in 1,3-dien-5-yne cycloaromatization. Preference for sterically hindered ortho-selective cyclization may be attributed to the formation of a transition state radical possessing more stable ortho-methoxy cyclohexadiene radical moiety (driving force).
The Baylis-Hillman acetates in organic synthesis: Unprecedented sodium nitrite induced intramolecular Friedel-Crafts cyclization of secondary nitro compounds
Basavaiah, Deevi,Reddy, Daggula Mallikarjuna
, p. 23966 - 23970 (2014/06/24)
Unprecedented sodium nitrite mediated intramolecular Friedel-Crafts cyclization of alkyl (E)-2-arylidene-4-nitroalkanoates and (E)-3-arylidene-5- nitroalkan-2-ones derived from Baylis-Hillman acetates, providing a facile protocol for synthesis of naphthal
Novel [4 + 2]-benzannulation to access substituted benzenes and polycyclic aromatic and benzene-fused heteroaromatic compounds
Raji Reddy, Chada,Dilipkumar, Uredi,Damoder Reddy, Motatipally
supporting information, p. 3792 - 3795 (2014/08/05)
A common [4 + 2]-benzannulation of Morita-Baylis-Hillman acetates of acetylenic aldehydes with boronic acids has been developed for the synthesis of aromatic and heteroaromatic compounds through tandem allylic substitution/hydroarylative cycloisomerization process. This method provides a facile and general route to substituted benzenes, naphthalenes, other polycyclic aromatics, and various benzene-fused heteroaromatic compounds such as benzofuran, benzothiophene, indole, and carbazoles.
