TY - JOUR
T1 - Synthesis of 2-Amino-2′-hydroxy-1,1′-biaryls via Cascade Benzannulation and C-N Bond Cleavage Sequence
AU - Adepu, Raju
AU - Dhanaji, Jadhav Rahul
AU - Samatha, Polasani
AU - Mainkar, Prathama S.
AU - Chandrasekhar, Srivari
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/11/6
Y1 - 2020/11/6
N2 - A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.
AB - A serendipitous synthesis of N-substituted 2-amino-2′-hydroxy-1,1′-biaryls through an aryne annulation with indolyl β-ketonitrile/ester in a cascade manner is demonstrated. The reaction sequence involves benzyne-mediated [2 + 2] Stoltz-type cycloaddition-cleavage and intramolecular Michael addition followed by C-N bond cleavage under transition-metal-free reaction conditions. Interestingly, while [4 + 2] Diels-Alder reaction is a possible pathway, no traces of the regioisomer was isolated.
UR - https://www.scopus.com/pages/publications/85095862322
U2 - 10.1021/acs.orglett.0c02749
DO - 10.1021/acs.orglett.0c02749
M3 - Article
C2 - 33081468
AN - SCOPUS:85095862322
SN - 1523-7060
VL - 22
SP - 8224
EP - 8228
JO - Organic Letters
JF - Organic Letters
IS - 21
ER -