BIOMAT Database Logo BIOMAT Database Logo

Multicomponent reaction for the first synthesis of 2,2-dialkyl- and 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines as scaffolds for various 3,4-dihydro-2H-1,3-thiazine derivatives. 2014

Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
Institut für Chemie, Carl von Ossietzky Universität Oldenburg, P. O. Box 2503, Carl-von-Ossietzky-Str. 9-11, 26111 Oldenburg, Germany. juergen.martens@uni-oldenburg.de.

A two-step sequence for the synthesis of various 3,4-dihydro-2H-1,3-thiazines is presented. In the first step, 2H-1,3-thiazines were prepared by a new multicomponent reaction (MCR). Starting from β-chlorovinyl aldehydes, this MCR offers an efficient and facile access to 2,2-dialkyl- and 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines. The potential of these products in subsequent reactions was verified by the conversion to 3,4-dihydro-2H-1,3-thiazine-containing bisamides, β-lactams, and methoxy amides.

UI MeSH Term Description Entries
D000447 Aldehydes Organic compounds containing a carbonyl group in the form -CHO. Aldehyde
D000577 Amides Organic compounds containing the -CO-NH2 radical. Amides are derived from acids by replacement of -OH by -NH2 or from ammonia by the replacement of H by an acyl group. (From Grant & Hackh's Chemical Dictionary, 5th ed) Amide
D013843 Thiazines
D047090 beta-Lactams Four-membered cyclic AMIDES, best known for the PENICILLINS based on a bicyclo-thiazolidine, as well as the CEPHALOSPORINS based on a bicyclo-thiazine, and including monocyclic MONOBACTAMS. The BETA-LACTAMASES hydrolyze the beta lactam ring, accounting for BETA-LACTAM RESISTANCE of infective bacteria. beta-Lactam,4-Thia-1-Azabicyclo(3.2.0)Heptanes,4-Thia-1-Azabicyclo(4.2.0)Octanes,beta Lactam,beta Lactams

Related Publications

Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
Thiazine derivatives. 3. The synthesis of some 2-substituted 5,6-dihydro-1,3(4H)-thiazines and tetrahydro-1,3-thiazines related to cephams.
February 1966, The Journal of organic chemistry,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
Multicomponent synthesis of 3,6-dihydro-2H-1,3-thiazine-2-thiones.
February 2012, Molecules (Basel, Switzerland),
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
Sulfonoketenimides as key intermediates for the synthesis of 2-thioxo-2H-1,3-thiazines and 2-arylimino-2H-1,3-thiazines.
November 2013, Molecular diversity,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
1,3-dihydro-1-methyl-5,6- (and 5,7-) diaryl-2H-1,4-diazepin-2-ones.
September 1969, Journal of medicinal chemistry,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
[New syntheses of 2-amino-5,6-dihydro-4H-1,3-thiazines].
October 1968, Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
Synthesis of 3,4-Dihydro-2H-1,3-thiazines from α-Enolic Dithioesters and 1,3,5-Triazinanes via a Formal (3 + 3) Annulation Reaction.
October 2020, The Journal of organic chemistry,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
Design and Synthesis of Fluorescent 1,3-Diaryl-β-carbolines and 1,3-Diaryl-3,4-dihydro-β-carbolines.
May 2021, ACS omega,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
[Synthesis of 1,3-dihydro-1,3-dioxo-2H-isoindole derivatives].
July 2008, Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
[Effect of 2-ADT (2-amino-5,6-dihydro-4H-1,3-thiazine) on the radiation reaction of hemopoietic organs].
January 1978, Radiobiologiia,
Fabian Brockmeyer, and Robin Schoemaker, and Marc Schmidtmann, and Jürgen Martens
[A new synthetic method of 3,4-fused 5,6-dihydro-2h-pyran derivatives].
June 1974, Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan,
Copied contents to your clipboard!