Direct Mannich and Nitro‐Mannich Reactions with Non‐Activated Imines: AgOTf‐Catalyzed Addition of Pronucleophiles to  ortho ‐Alkynylaryl Aldimines Leading to 1,2‐Dihydroisoquinolines | Zendy

Asao Naoki | Zendy; Yudha S. Salprima | Zendy; Nogami Tsutomu | Zendy; Yamamoto Yoshinori | Zendy

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Direct Mannich and Nitro‐Mannich Reactions with Non‐Activated Imines: AgOTf‐Catalyzed Addition of Pronucleophiles to ortho ‐Alkynylaryl Aldimines Leading to 1,2‐Dihydroisoquinolines

Author(s) -

Asao Naoki,

Yudha S. Salprima,

Nogami Tsutomu,

Yamamoto Yoshinori

Publication year - 2005

Publication title -

angewandte chemie international edition

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 5.831

H-Index - 550

eISSN - 1521-3773

pISSN - 1433-7851

DOI - 10.1002/anie.200500795

Subject(s) - aldimine , protonation , nitro , catalysis , chemistry , stoichiometry , medicinal chemistry , combinatorial chemistry , organic chemistry , ion , alkyl

A variety of 1,2‐dihydroisoquinoline derivatives 3 have been prepared in good to high yields by the AgOTf‐catalyzed reaction of ortho ‐alkynylaryl aldimines 1 with various pronucleophiles 2 (see scheme). Treatment of 1 with a stoichiometric amount of AgOTf followed by protonation with TfOH produced 4 , which suggests the formation of an isoquinolinium intermediate in the present direct addition reaction. Tf=trifluoromethanesulfonyl.

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