Direct Mannich and nitro-Mannich reactions with non-activated imines: AgOTF-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines

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

doi:10.1002/anie.200500795

Direct Mannich and nitro-Mannich reactions with non-activated imines: AgOTF-catalyzed addition of pronucleophiles to ortho-alkynylaryl aldimines leading to 1,2-dihydroisoquinolines

Naoki Asao, Salprima Yudha S., Tsutomu Nogami, Yoshinori Yamamoto

Research output: Contribution to journal › Article › peer-review

213 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	5526-5528
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	44
Issue number	34
DOIs	https://doi.org/10.1002/anie.200500795
Publication status	Published - 2005 Sep 2

Keywords

Imines
Mannich reaction
Nitrogen heterocycles
Pronucleophiles
Synthetic methods

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200500795

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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. / Asao, Naoki; Yudha S., Salprima; Nogami, Tsutomu; Yamamoto, Yoshinori.

In: Angewandte Chemie - International Edition, Vol. 44, No. 34, 02.09.2005, p. 5526-5528.

Research output: Contribution to journal › Article › peer-review

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keywords = "Imines, Mannich reaction, Nitrogen heterocycles, Pronucleophiles, Synthetic methods",

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AU - Asao, Naoki

AU - Yudha S., Salprima

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AU - Yamamoto, Yoshinori

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AB - (Chemical Equation Presented) 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.

KW - Imines

KW - Mannich reaction

KW - Nitrogen heterocycles

KW - Pronucleophiles

KW - Synthetic methods

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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

Abstract

Keywords

ASJC Scopus subject areas

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