Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates

K E Judd; Mary F Mahon; Lorenzo Caggiano

doi:10.1055/s-0029-1216904

Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates

K E Judd, Mary F Mahon, Lorenzo Caggiano

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31 Citations (SciVal)

Abstract

An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF3 center dot OEt2 to generate various lactams, including tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives.

Original language	English
Pages (from-to)	2809-2817
Number of pages	9
Journal	Synthesis
Volume	2009
Issue number	16
Early online date	13 Jul 2009
DOIs	https://doi.org/10.1055/s-0029-1216904
Publication status	Published - Aug 2009

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title = "Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates",

abstract = "An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF3 center dot OEt2 to generate various lactams, including tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives.",

author = "Judd, \{K E\} and Mahon, \{Mary F\} and Lorenzo Caggiano",

year = "2009",

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doi = "10.1055/s-0029-1216904",

language = "English",

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T1 - Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates

AU - Judd, K E

AU - Mahon, Mary F

AU - Caggiano, Lorenzo

PY - 2009/8

Y1 - 2009/8

N2 - An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF3 center dot OEt2 to generate various lactams, including tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives.

AB - An efficient one-pot procedure is described in which an isocyanate intermediate, generated from the corresponding carboxylic acid by a modified Curtius rearrangement, is captured by a tethered aromatic ring in the presence of BF3 center dot OEt2 to generate various lactams, including tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives.

UR - https://www.scopus.com/pages/publications/70449372103

UR - http://dx.doi.org/10.1055/s-0029-1216904

U2 - 10.1055/s-0029-1216904

DO - 10.1055/s-0029-1216904

M3 - Article

SN - 0039-7881

VL - 2009

SP - 2809

EP - 2817

JO - Synthesis

JF - Synthesis

IS - 16

ER -

Efficient synthesis of tetrahydro-β-carbolin-1-one and dihydroisoquinolin-1-one derivatives as versatile intermediates

Abstract

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