Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

Art Kruithof; Jos R. Mulder; J. M. Ruiz; Elwin Janssen; M. Mooijman; Eelco Ruijter; Célia Fonseca Guerra; F. Matthias Bickelhaupt; Romano V.A. Orru

doi:10.1002/ejoc.201700941

Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

Art Kruithof, Jos R. Mulder, J. M. Ruiz, Elwin Janssen, M. Mooijman, Eelco Ruijter, Célia Fonseca Guerra, F. Matthias Bickelhaupt, Romano V.A. Orru

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

2 Citations (Scopus)

Abstract

Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.

Original language	English
Pages (from-to)	104-112
Number of pages	9
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	1
DOIs	https://doi.org/10.1002/ejoc.201700941
Publication status	Published - 10 Jan 2018
Externally published	Yes

Keywords

Computer chemistry
Density functional calculations
Multicomponent reactions
Nitrogen heterocycles
Synthesis design

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry

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10.1002/ejoc.201700941

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title = "Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones",

abstract = "Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.",

keywords = "Computer chemistry, Density functional calculations, Multicomponent reactions, Nitrogen heterocycles, Synthesis design",

author = "Art Kruithof and Mulder, \{Jos R.\} and Ruiz, \{J. M.\} and Elwin Janssen and M. Mooijman and Eelco Ruijter and \{Fonseca Guerra\}, C{\'e}lia and Bickelhaupt, \{F. Matthias\} and Orru, \{Romano V.A.\}",

note = "Publisher Copyright: {\textcopyright} 2018 WILEY-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2018",

month = jan,

day = "10",

doi = "10.1002/ejoc.201700941",

language = "English",

volume = "2018",

pages = "104--112",

journal = "European Journal of Organic Chemistry",

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publisher = "Wiley-VCH Verlag",

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T1 - Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

AU - Kruithof, Art

AU - Mulder, Jos R.

AU - Ruiz, J. M.

AU - Janssen, Elwin

AU - Mooijman, M.

AU - Ruijter, Eelco

AU - Fonseca Guerra, Célia

AU - Bickelhaupt, F. Matthias

AU - Orru, Romano V.A.

PY - 2018/1/10

Y1 - 2018/1/10

N2 - Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.

AB - Predicting reactivity in multicomponent reactions (MCRs) is extremely difficult. These reactions proceed by multiple pathways and are inherently associated with a potentially large variation of reactants and functional groups. To date, theoretical chemistry has been used in hindsight to verify experimental observations. However, its use in the early stages of the development of a (multicomponent) reaction process can prevent laborious and time-consuming optimization studies by pinpointing the most relevant parameter(s) in the reactivity, thus focusing experimental efforts. Herein, we discuss a study that truly integrates theoretical and synthetic chemistry to unravel in full detail the complex and intricate reaction characteristics of the novel versatile MCR of α-acidic iso(thio)cyanates, amines and aldehydes to access densely functionalized imidazoline-2-(thi)ones.

KW - Computer chemistry

KW - Density functional calculations

KW - Multicomponent reactions

KW - Nitrogen heterocycles

KW - Synthesis design

UR - https://www.scopus.com/pages/publications/85040246554

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DO - 10.1002/ejoc.201700941

M3 - Article

AN - SCOPUS:85040246554

SN - 1434-193X

VL - 2018

SP - 104

EP - 112

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 1

ER -

Integrative Theory/Experiment-Driven Exploration of a Multicomponent Reaction towards Imidazoline-2-(thi)ones

Abstract

Keywords

ASJC Scopus subject areas

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