volume 16 issue 10 pages 543-550

Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction

Konstantin A. Frolov 1
Tatyana M Pekhtereva 3
Olena S Papaianina 3
Sergey Yu Suykov 3
Publication typeJournal Article
Publication date2014-09-23
SJR
CiteScore
Impact factor
ISSN21568952, 21568944
PubMed ID:  25191927
General Chemistry
General Medicine
Abstract
This Research Article describes the synthesis of an over 700-member library of (8R/8S)-3-R-8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazin-9-carbonitriles by uncatalyzed Mannich-type reaction of N-methylmorpholinium (4R/4S)-4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-thiolates with a set of primary amines and excessive HCHO. The scope and limitations of the reaction were studied. Starting thiolates were obtained in yields of 53-82% by multicomponent reaction of aromatic aldehydes, cyanothioacetamide, 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid), and N-methylmorpholine, followed by heterocyclization of the resulting Michael adducts.
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GOST |
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GOST Copy
Dotsenko V. V. et al. Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction // ACS Combinatorial Science. 2014. Vol. 16. No. 10. pp. 543-550.
GOST all authors (up to 50) Copy
Dotsenko V. V., Frolov K. A., Pekhtereva T. M., Papaianina O. S., Suykov S. Yu., Krivokolysko S. G. Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction // ACS Combinatorial Science. 2014. Vol. 16. No. 10. pp. 543-550.
RIS |
Cite this
RIS Copy
TY - JOUR
DO - 10.1021/co5000807
UR - https://doi.org/10.1021/co5000807
TI - Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction
T2 - ACS Combinatorial Science
AU - Dotsenko, Viktor V
AU - Frolov, Konstantin A.
AU - Pekhtereva, Tatyana M
AU - Papaianina, Olena S
AU - Suykov, Sergey Yu
AU - Krivokolysko, Sergey G.
PY - 2014
DA - 2014/09/23
PB - American Chemical Society (ACS)
SP - 543-550
IS - 10
VL - 16
PMID - 25191927
SN - 2156-8952
SN - 2156-8944
ER -
BibTex |
Cite this
BibTex (up to 50 authors) Copy
@article{2014_Dotsenko,
author = {Viktor V Dotsenko and Konstantin A. Frolov and Tatyana M Pekhtereva and Olena S Papaianina and Sergey Yu Suykov and Sergey G. Krivokolysko},
title = {Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction},
journal = {ACS Combinatorial Science},
year = {2014},
volume = {16},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://doi.org/10.1021/co5000807},
number = {10},
pages = {543--550},
doi = {10.1021/co5000807}
}
MLA
Cite this
MLA Copy
Dotsenko, Viktor V., et al. “Design and Synthesis of Pyrido[2,1-b][1,3,5]thiadiazine Library via Uncatalyzed Mannich-Type Reaction.” ACS Combinatorial Science, vol. 16, no. 10, Sep. 2014, pp. 543-550. https://doi.org/10.1021/co5000807.