Tetrahedron

, volume 54 , issue 40 , pages 12361-12378

Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones

Izaskun Manteca ¹

Begoña Etxarri ¹

Ainhoa Ardeo ¹

Sonia Arrasate ¹

Iñaki Osante ¹

Nuria Sotomayor ¹

E. Lete ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

Departamento de Quı́mica Orgánica, Facultad de Ciencias, Universidad del Paı́s Vasco, Apdo. 644, 48080 Bilbao, Spain |

Publication type: Journal Article

Publication date: 1998-10-01

Elsevier

Tetrahedron

scimago Q3

wos Q2

SJR: 0.426

CiteScore: 4.1

Impact factor: 2.2

ISSN: 00404020, 14645416

DOI: 10.1016/S0040-4020(98)00745-5

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Organic Chemistry

Drug Discovery

Biochemistry

Abstract

A procedure for producing 1,4-dianion equivalents consists of reductive lithiation, induced by 4,4.-di- tert -butylbiphenylide, of functionalized phenyl sulfides. Nucleophilic addition of 4-lithio-2-(trimethylsilylmethyl)but-1-ene 1 and 2-(3-lithiopropyl)-2-trimethylsilyl-1,3-dithiane 2 thus prepared to N -phenethyl- cis -norbor-5-en-2,3-dicarboximide 9 afforded the corresponding α-hydroxy lactams in good yields. Besides, access to C-10b substituted α,β-unsaturated pyrroloisoquinolinones 3 was efficiently achieved via a tandem organolithium nucleophilic addition — N -acyliminium ion cyclization sequence and subsequent retro Diels-Alder reaction. The methodology can be extended to functionalized organolithiums, but the N -acyliminium cyclization fails if the allylsilane moiety is present. Graphic

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Manteca I. et al. Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones // Tetrahedron. 1998. Vol. 54. No. 40. pp. 12361-12378.

GOST all authors (up to 50) Copy

Manteca I., Etxarri B., Ardeo A., Arrasate S., Osante I., Sotomayor N., Lete E. Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones // Tetrahedron. 1998. Vol. 54. No. 40. pp. 12361-12378.

RIS |

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RIS Copy

TY - JOUR

DO - 10.1016/S0040-4020(98)00745-5

UR - https://doi.org/10.1016/S0040-4020(98)00745-5

TI - Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones

T2 - Tetrahedron

AU - Manteca, Izaskun

AU - Etxarri, Begoña

AU - Ardeo, Ainhoa

AU - Arrasate, Sonia

AU - Osante, Iñaki

AU - Sotomayor, Nuria

AU - Lete, E.

PY - 1998

DA - 1998/10/01

PB - Elsevier

SP - 12361-12378

IS - 40

VL - 54

SN - 0040-4020

SN - 1464-5416

ER -

BibTex |

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@article{1998_Manteca,

author = {Izaskun Manteca and Begoña Etxarri and Ainhoa Ardeo and Sonia Arrasate and Iñaki Osante and Nuria Sotomayor and E. Lete},

title = {Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones},

journal = {Tetrahedron},

year = {1998},

volume = {54},

publisher = {Elsevier},

month = {oct},

url = {https://doi.org/10.1016/S0040-4020(98)00745-5},

number = {40},

pages = {12361--12378},

doi = {10.1016/S0040-4020(98)00745-5}

}

MLA

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MLA Copy

Manteca, Izaskun, et al. “Functionalized organolithium compounds: Generation via reductive lithiation and nucleophilic addition to N-phenethylimides. Access to functionalized dihydropyrrolo[2,1-a]isoquinolinones.” Tetrahedron, vol. 54, no. 40, Oct. 1998, pp. 12361-12378. https://doi.org/10.1016/S0040-4020(98)00745-5.

Publisher

Elsevier

Journal

Tetrahedron

scimago Q3

wos Q2

SJR

0.426

CiteScore

4.1

Impact factor

2.2

ISSN

00404020 (Print)

14645416 (Electronic)