Università degli Studi di Urbino Carlo Bo / Portale Web di Ateneo


MULTICOMPONENT REACTIONS IN ORGANIC SYNTHESIS
MULTICOMPONENT REACTIONS IN ORGANIC SYNTHESIS

A.Y. Credits
2021/2022 4
Lecturer Email Office hours for students
Fabio Mantellini Every day by appointment.
Teaching in foreign languages
Course entirely taught in a foreign language English
This course is entirely taught in a foreign language and the final exam can be taken in the foreign language.

Assigned to the Degree Course

Research Methods in Science and Technology (XXXVII)
Curriculum: PERCORSO COMUNE
Date Time Classroom / Location
Date Time Classroom / Location

Learning Objectives

The course is organized as a study of the main multicomponent reactions used in the organic synthesis of scaffolds of pharmacological and medicinal interest. The advantages related to the use of these approaches will be discussed in a vision of sustainable and low environmental impact chemistry.

Program

Introduction to the course, Explanation of the Examination modalities, Definition of Ideal Synthesis, Linear synthesis, Multicomponent reactions,. Definitions, classifications, Basic characteristics of modern multicomponent reactions: Convergence, Parallel approaches, Sustainability, Waste prevention, Atom economy, Safe chemicals design, Benign solvents and auxiliaries, Energy efficiency, Renewable feedstocks, Catalysis, Inherently safe chemistry for accident prevention, Chemical Space (Theoretical spaces, Empirical spaces), Scaffold place, Complexity generation, Diversity generation.

Classical MCRs

Hystory: Laurent and Gerhardt Reaction; The Strecker synthesis: General Aspects, purpose and applications, mechanism, green variants. The Petasis reaction: General Aspects, purpose and applications, mechanism. The Gewald reaction: General Aspects, purpose and applications, mechanism. The Asinger reaction: General Aspects, purpose and applications, mechanism. The Mannich reaction: General Aspects, purpose and applications, mechanism. The Biginelli reaction: General Aspects, purpose and applications, mechanism. The Hantzsch pyridine synthesis: General Aspects, purpose and applications, mechanism. The Passerini reaction: General Aspects, purpose and applications, mechanism. The 3CR Ugi Reactions: General Aspects, purpose and applications, mechanism. The 4CR Ugi Reactions: General Aspects, purpose and applications, mechanism. The Ugi Tetrazole 4CR Synthesis: General Aspects, purpose and applications, mechanism. The Groebke-Blackburn-Bienaymè reaction: General Aspects, purpose and applications, mechanism. The van Leusen Imidazole Synthesis: General Aspects, purpose and applications, mechanism.

1,2-Diaza-1,3 Dienes: Powerful Tools for MCR

Structural Diversity and Molecular Complexity: Synthesis of novel indole-based scaffolds by different assembly of tryptamines, azoenes, and aldehydes.

Regiochemical Diversity: Zinc(II) Triflate- Catalyzed Synthesis of polyfunctionalyzed Pyrroles, Synthesis of Functionalized Pyrroles via Catalyst and Solvent-Free Sequentila Thre- Component Enamine-Azoene Annulation.

Skeleton Diversity: One-Pot, Three Component Synthesis of 5-Hydrazinoalkylidene Rhodanines, Approaches to Heterocyclic Skeletal Diversity by Sequential Three-component Reaction of amines, Isothiocyanates, and 1,2-diaza-1,3-dienes.

Scaffold Diversity: Tandem Aza-Wittig/Carbodiimide-Mediated Annulation Applicable to 1,2-diaza-1,3-denes for the One-Pot Synthesis of fully Substituted 1,2-Diaminoimidazoles.

Teaching Material

The teaching material prepared by the lecturer in addition to recommended textbooks (such as for instance slides, lecture notes, exercises, bibliography) and communications from the lecturer specific to the course can be found inside the Moodle platform › blended.uniurb.it

Teaching, Attendance, Course Books and Assessment

Assessment

The candidate must produce a paper that summarizes the salient data described in a scientific publication concerning multicomponent reactions in the field of organic chemistry.

Disabilità e DSA

Le studentesse e gli studenti che hanno registrato la certificazione di disabilità o la certificazione di DSA presso l'Ufficio Inclusione e diritto allo studio, possono chiedere di utilizzare le mappe concettuali (per parole chiave) durante la prova di esame.

A tal fine, è necessario inviare le mappe, due settimane prima dell’appello di esame, alla o al docente del corso, che ne verificherà la coerenza con le indicazioni delle linee guida di ateneo e potrà chiederne la modifica.

Additional Information for Non-Attending Students

Assessment

The candidate must produce a paper that summarizes the salient data described in a scientific publication concerning multicomponent reactions in the field of organic chemistry.

Disabilità e DSA

Le studentesse e gli studenti che hanno registrato la certificazione di disabilità o la certificazione di DSA presso l'Ufficio Inclusione e diritto allo studio, possono chiedere di utilizzare le mappe concettuali (per parole chiave) durante la prova di esame.

A tal fine, è necessario inviare le mappe, due settimane prima dell’appello di esame, alla o al docente del corso, che ne verificherà la coerenza con le indicazioni delle linee guida di ateneo e potrà chiederne la modifica.

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