Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one

Shobanbabu Bommagani; Na Ra Lee; Xuan Zhang; Linda P. Dwoskin; Guangrong Zheng

doi:10.1016/j.tetlet.2015.09.156

Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one

Shobanbabu Bommagani, Na Ra Lee, Xuan Zhang, Linda P. Dwoskin, Guangrong Zheng

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

1 Scopus citations

Abstract

Efficient syntheses of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one are presented. The O-alkylated analogues were synthesized through a reduction-cyclization cascade and a selective O-alkylation reaction; whereas the N-alkylated analogues were obtained through a key Buchwald coupling.

Original language	English
Pages (from-to)	6472-6474
Number of pages	3
Journal	Tetrahedron Letters
Volume	56
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2015.09.156
State	Published - Nov 18 2015

Bibliographical note

Publisher Copyright:
© 2015 Elsevier Ltd.

Funding

This work was supported by funding from the National Institute of Health ( DA030667 and UL1 TR000117 ).

Funders	Funder number
Italian National Health Institute	DA030667, UL1 TR000117

Keywords

1,2,3,4-Tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one
Buchwald coupling
Muscarinic acetylcholine receptors
Reduction-cyclization cascade
Suzuki coupling

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2015.09.156

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title = "Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one",

abstract = "Efficient syntheses of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one are presented. The O-alkylated analogues were synthesized through a reduction-cyclization cascade and a selective O-alkylation reaction; whereas the N-alkylated analogues were obtained through a key Buchwald coupling.",

keywords = "1,2,3,4-Tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one, Buchwald coupling, Muscarinic acetylcholine receptors, Reduction-cyclization cascade, Suzuki coupling",

author = "Shobanbabu Bommagani and Lee, \{Na Ra\} and Xuan Zhang and Dwoskin, \{Linda P.\} and Guangrong Zheng",

note = "Publisher Copyright: {\textcopyright} 2015 Elsevier Ltd.",

year = "2015",

month = nov,

day = "18",

doi = "10.1016/j.tetlet.2015.09.156",

language = "English",

volume = "56",

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T1 - Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one

AU - Bommagani, Shobanbabu

AU - Lee, Na Ra

AU - Zhang, Xuan

AU - Dwoskin, Linda P.

AU - Zheng, Guangrong

PY - 2015/11/18

Y1 - 2015/11/18

N2 - Efficient syntheses of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one are presented. The O-alkylated analogues were synthesized through a reduction-cyclization cascade and a selective O-alkylation reaction; whereas the N-alkylated analogues were obtained through a key Buchwald coupling.

AB - Efficient syntheses of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one are presented. The O-alkylated analogues were synthesized through a reduction-cyclization cascade and a selective O-alkylation reaction; whereas the N-alkylated analogues were obtained through a key Buchwald coupling.

KW - 1,2,3,4-Tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one

KW - Buchwald coupling

KW - Muscarinic acetylcholine receptors

KW - Reduction-cyclization cascade

KW - Suzuki coupling

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U2 - 10.1016/j.tetlet.2015.09.156

DO - 10.1016/j.tetlet.2015.09.156

M3 - Article

AN - SCOPUS:84946233370

SN - 0040-4039

VL - 56

SP - 6472

EP - 6474

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 46

ER -

Synthesis of O- and N-alkylated products of 1,2,3,4-tetrahydrobenzo[c][2,7]naphthyrin-5(6H)-one

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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