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MULTICOMPONENT REACTIONS IN ORGANIC SYNTHESIS
MULTICOMPONENT REACTIONS IN ORGANIC SYNTHESIS

A.Y. Credits
2022/2023 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 (XXXVIII)
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. Applications: synthesis of Carfentanil, Reserpine,  Saxagliptin, Clopidogrel, Bucherer-Bergs reaction: General Aspects, purpose and applications, mechanism, green variants. Applications: Synthesis  of Phenytoin, Sorinil. The Gewald reaction: General Aspects, purpose and applications, mechanism. Synthesis of Olanzapine, Tinoridine. Applications: Synthesis  of 2,5-dihydro-thiophenes from 1,2-diaza-1,3-dienesThe Mannich reaction: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Tramadol, Atropine, Ezetimibe.  The Petasis reaction: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Zanamivir. Povarov reaction: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of EMD534085. Doebner reaction: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Brequinar. The Hantzsch pyridine synthesis: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Felodipine. The Hantzsch pyrrole synthesis: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Atorvastatin.  The Asinger reaction: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of D-Penicillamine. The Passerini reaction: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Propranolol, desacetoxytubulysin H, The 3CR Ugi Reactions: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Xylocaine.  The 4CR Ugi Reactions: General Aspects, purpose and applications, mechanism. Applications: Synthesis  of Carfentanil, Aplaviroc. The Ugi Tetrazole 4CR Synthesis: General Aspects, purpose and applications, mechanism. The van Leusen Imidazole Synthesis: General Aspects, purpose and applications, mechanism.  Applications: Synthesis  of SB220025. The Groebke-Blackburn-Bienaymè reaction: General Aspects, purpose and applications, mechanism. The Biginelli reaction: General Aspects, purpose and applications, mechanism. Examples of Combination of Multicomponent Reactions: Applications: Synthesis  of penicillin, Telaprevir, Tubugis.

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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