Real Multicomponent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles

Frank Richter; Jennifer Seifert; Marcus Korb; Heinrich Lang; Klaus Banert

doi:10.1002/ejoc.201800701

Real Multicomponent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles

Frank Richter, Jennifer Seifert, Marcus Korb, Heinrich Lang, Klaus Banert

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

11 Citations (Web of Science)

Abstract

Allenyl isothiocyanates, which can be easily generated by flash vacuum pyrolysis, are known to readily form 1,3-thiazoles with various nucleophiles. This is also true for heterocyclic aromatic amines and sterically hindered amines that are in other aspects used as non-nucleophilic bases. The chemistry of these synthetically useful cumulenes is now expanded to the field of multicomponent reactions with the mentioned amines and selected electrophiles. In an efficient, catalyst-free three-component reaction (3-CR) sequence, highly substituted heterocyclic compounds are formed containing the 2-amino-1,3-thiazole skeleton. The reaction conditions and mechanisms leading to these potentially bioactive molecules were investigated and optimized for the synthesis of a small compound library.

Original language	English
Pages (from-to)	4673-4682
Number of pages	10
Journal	European Journal of Organic Chemistry
Volume	2018
Issue number	34
DOIs	https://doi.org/10.1002/ejoc.201800701
Publication status	Published - 16 Sept 2018
Externally published	Yes

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title = "Real Multicomponent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles",

abstract = "Allenyl isothiocyanates, which can be easily generated by flash vacuum pyrolysis, are known to readily form 1,3-thiazoles with various nucleophiles. This is also true for heterocyclic aromatic amines and sterically hindered amines that are in other aspects used as non-nucleophilic bases. The chemistry of these synthetically useful cumulenes is now expanded to the field of multicomponent reactions with the mentioned amines and selected electrophiles. In an efficient, catalyst-free three-component reaction (3-CR) sequence, highly substituted heterocyclic compounds are formed containing the 2-amino-1,3-thiazole skeleton. The reaction conditions and mechanisms leading to these potentially bioactive molecules were investigated and optimized for the synthesis of a small compound library.",

keywords = "C-C coupling, Cyclization, Heterocycles, Multicomponent reactions, Thiazoles, DIELS-ALDER REACTIONS, FUNCTIONALIZED THIAZOLES, ALLENYL ISOTHIOCYANATES, REARRANGEMENT REACTIONS, ORGANIC-CHEMISTRY, DERIVATIVES, DISCOVERY, INHIBITORS, ATTACK, TRANSFORMATIONS",

author = "Frank Richter and Jennifer Seifert and Marcus Korb and Heinrich Lang and Klaus Banert",

year = "2018",

month = sep,

day = "16",

doi = "10.1002/ejoc.201800701",

language = "English",

volume = "2018",

pages = "4673--4682",

journal = "European Journal of Organic Chemistry",

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number = "34",

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TY - JOUR

T1 - Real Multicomponent Reactions

T2 - Synthesis of Highly Substituted 2-Aminothiazoles

AU - Richter, Frank

AU - Seifert, Jennifer

AU - Korb, Marcus

AU - Lang, Heinrich

AU - Banert, Klaus

PY - 2018/9/16

Y1 - 2018/9/16

N2 - Allenyl isothiocyanates, which can be easily generated by flash vacuum pyrolysis, are known to readily form 1,3-thiazoles with various nucleophiles. This is also true for heterocyclic aromatic amines and sterically hindered amines that are in other aspects used as non-nucleophilic bases. The chemistry of these synthetically useful cumulenes is now expanded to the field of multicomponent reactions with the mentioned amines and selected electrophiles. In an efficient, catalyst-free three-component reaction (3-CR) sequence, highly substituted heterocyclic compounds are formed containing the 2-amino-1,3-thiazole skeleton. The reaction conditions and mechanisms leading to these potentially bioactive molecules were investigated and optimized for the synthesis of a small compound library.

AB - Allenyl isothiocyanates, which can be easily generated by flash vacuum pyrolysis, are known to readily form 1,3-thiazoles with various nucleophiles. This is also true for heterocyclic aromatic amines and sterically hindered amines that are in other aspects used as non-nucleophilic bases. The chemistry of these synthetically useful cumulenes is now expanded to the field of multicomponent reactions with the mentioned amines and selected electrophiles. In an efficient, catalyst-free three-component reaction (3-CR) sequence, highly substituted heterocyclic compounds are formed containing the 2-amino-1,3-thiazole skeleton. The reaction conditions and mechanisms leading to these potentially bioactive molecules were investigated and optimized for the synthesis of a small compound library.

KW - C-C coupling

KW - Cyclization

KW - Heterocycles

KW - Multicomponent reactions

KW - Thiazoles

KW - DIELS-ALDER REACTIONS

KW - FUNCTIONALIZED THIAZOLES

KW - ALLENYL ISOTHIOCYANATES

KW - REARRANGEMENT REACTIONS

KW - ORGANIC-CHEMISTRY

KW - DERIVATIVES

KW - DISCOVERY

KW - INHIBITORS

KW - ATTACK

KW - TRANSFORMATIONS

U2 - 10.1002/ejoc.201800701

DO - 10.1002/ejoc.201800701

M3 - Article

SN - 1434-193X

VL - 2018

SP - 4673

EP - 4682

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 34

ER -

Real Multicomponent Reactions: Synthesis of Highly Substituted 2-Aminothiazoles

Abstract

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