Synthesis of N,N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines as a quinodimethane precursor by the reaction of N,N-dimethyl- N-(tributylstannyl)methyl-4-substituted benzylammonium salts with lithium diisopropylamide

Yasuhiro Maeda; Yoshiro Sato

doi:10.1248/cpb.46.508

Synthesis of N,N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines as a quinodimethane precursor by the reaction of N,N-dimethyl- N-(tributylstannyl)methyl-4-substituted benzylammonium salts with lithium diisopropylamide

Yasuhiro Maeda
, Yoshiro Sato

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

6 Citations (Scopus)

Abstract

Reaction of N,N-dimethyl-N-(tributylstannyl)methyl-4-substituted benzylammonium salts 2 with lithium diisopropylamide (LDA) gave N,N-dimethyl- 2-(tributylstannyl)methyl-5-substituted benzylamines 3 as the main products. Treatment of 3 with iodomethane followed by tetrabutylammonium fluoride (TBAF) in the presence of dimethyl fumarate gave the corresponding dimethyl trans-1,2,3,4-tetrahydro-6-substituted naphthalene-2,3-dicarboxylates 15 in good yields.

Original language	English
Pages (from-to)	508-511
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	46
Issue number	3
DOIs	https://doi.org/10.1248/cpb.46.508
Publication status	Published - 1998
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry
Drug Discovery

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title = "Synthesis of N,N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines as a quinodimethane precursor by the reaction of N,N-dimethyl- N-(tributylstannyl)methyl-4-substituted benzylammonium salts with lithium diisopropylamide",

abstract = "Reaction of N,N-dimethyl-N-(tributylstannyl)methyl-4-substituted benzylammonium salts 2 with lithium diisopropylamide (LDA) gave N,N-dimethyl- 2-(tributylstannyl)methyl-5-substituted benzylamines 3 as the main products. Treatment of 3 with iodomethane followed by tetrabutylammonium fluoride (TBAF) in the presence of dimethyl fumarate gave the corresponding dimethyl trans-1,2,3,4-tetrahydro-6-substituted naphthalene-2,3-dicarboxylates 15 in good yields.",

author = "Yasuhiro Maeda and Yoshiro Sato",

year = "1998",

doi = "10.1248/cpb.46.508",

language = "English",

volume = "46",

pages = "508--511",

journal = "Chemical and Pharmaceutical Bulletin",

issn = "0009-2363",

publisher = "Pharmaceutical Society of Japan",

number = "3",

}

Synthesis of N,N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines as a quinodimethane precursor by the reaction of N,N-dimethyl- N-(tributylstannyl)methyl-4-substituted benzylammonium salts with lithium diisopropylamide. / Maeda, Yasuhiro; Sato, Yoshiro.
In: Chemical and Pharmaceutical Bulletin, Vol. 46, No. 3, 1998, p. 508-511.

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

TY - JOUR

T1 - Synthesis of N,N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines as a quinodimethane precursor by the reaction of N,N-dimethyl- N-(tributylstannyl)methyl-4-substituted benzylammonium salts with lithium diisopropylamide

AU - Maeda, Yasuhiro

AU - Sato, Yoshiro

PY - 1998

Y1 - 1998

N2 - Reaction of N,N-dimethyl-N-(tributylstannyl)methyl-4-substituted benzylammonium salts 2 with lithium diisopropylamide (LDA) gave N,N-dimethyl- 2-(tributylstannyl)methyl-5-substituted benzylamines 3 as the main products. Treatment of 3 with iodomethane followed by tetrabutylammonium fluoride (TBAF) in the presence of dimethyl fumarate gave the corresponding dimethyl trans-1,2,3,4-tetrahydro-6-substituted naphthalene-2,3-dicarboxylates 15 in good yields.

AB - Reaction of N,N-dimethyl-N-(tributylstannyl)methyl-4-substituted benzylammonium salts 2 with lithium diisopropylamide (LDA) gave N,N-dimethyl- 2-(tributylstannyl)methyl-5-substituted benzylamines 3 as the main products. Treatment of 3 with iodomethane followed by tetrabutylammonium fluoride (TBAF) in the presence of dimethyl fumarate gave the corresponding dimethyl trans-1,2,3,4-tetrahydro-6-substituted naphthalene-2,3-dicarboxylates 15 in good yields.

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DO - 10.1248/cpb.46.508

M3 - Article

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SN - 0009-2363

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EP - 511

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 3

ER -

Synthesis of N,N-dimethyl-2-(tributylstannyl)methyl-5-substituted benzylamines as a quinodimethane precursor by the reaction of N,N-dimethyl- N-(tributylstannyl)methyl-4-substituted benzylammonium salts with lithium diisopropylamide

Abstract

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