Abstract
Alkyl (Z)-3-((2-(N-((E)-3-methoxy-3-oxoprop-1-en-1-yl)acetamido)phenyl)thio)acrylates are obtained from the reaction between 2-methylbenzothiazole and alkyl propiolates in 70% aqueous alcohol, in moderate yields. When dialkyl acetylenedicarboxylates were used under similar conditions, tetra-alkyl 9,10-dihydrobenzo[4,5]thiazolo[3,2-a]azepine-7,8,9,10-tetracarboxylates, together with dialkyl 4-acetyl-3,4-dihydro-2H-benzo[b][1,4]thiazine-2,3-dicarboxylates were obtained in about 4:1 ratios. The stereochemistry of these products has been confirmed by X-ray diffraction.
Graphical Abstract
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Wang K, Guengerich FP (2012) Bioactivation of fluorinated 2-aryl-benzothiazole antitumor molecules by human cytochrome P450s 1A1 and 2W1 and deactivation by cytochrome P450 2S1. Chem Res Toxicol 25:1740–1751. doi:10.1021/tx3001994
Huang Q, Mao J, Wan B, Wang Y, Brun R, Franzblau SG, Kozikowski AP (2009) Searching for new cures for tuberculosis: design, synthesis, and biological evaluation of 2-methylbenzothiazoles. J Med Chem 52:6757–6767. doi:10.1021/jm901112f
Singh M, Singh SK, Gangwar M, Nath G, Singh SK (2014) Design, synthesis and mode of action of some benzothiazole derivatives bearing an amide moiety as antibacterial agents. RSC Adv 4:19013–19023. doi:10.1039/C4RA02649G
Suresh CH, Rao JV, Jayaveera KN, Subudhi SK (2011) Synthesis and anthelmintic activity of 3-(2-hydrozino benzothiazole)-substituted indole-2-one. Int J Pharma 2:257–261
Rangappa S, Keri MR, Patil SA, Patil SB (2015) A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry. Eur J Med Chem 89:207–251. doi:10.1016/j.ejmech.2014.10.059
Yavari I, Sabbaghan M, Porshamsian K, Bagheri M, Ali-Asgari S, Hossaini Z (2007) Efficient synthesis of alkyl 2-[2-(arylcarbonylimino)-3-aryl-4-oxo-1,3-thiazolan-5-ylidene]-acetates. Mol Divers 11:81–85. doi:10.1007/s11030-007-9061-9
Yavari I, Hossain Z, Souri S, Seyfi S (2009) Diastereoselective synthesis of fused [1,3]thiazolo[1,3]oxazins and [1,3]oxazino[2,3-b][1,3]benzothiazoles. Mol Divers 13:439–443. doi:10.1007/s11030-009-9128-x
Yavari I, Shirgahi-Talari F, Hossaini Z, Sabbaghan M, Seyfi S (2010) Synthesis of functionalized 1,2,4-triazole-3-thiones from ammonium isothiocyanate, acid chlorides, and arylhydrazines. Mol Divers 14:763–766. doi:10.1007/s11030-009-9218-9
Yavari I, Sirouspour M, Souri S (2010) One-pot synthesis of functionalized 4-oxo-2-thioxo-1,3-thiazinanes from primary amines, \(\text{ CS }_{2}\), and itaconic anhydride. Mol Divers 14:611–615. doi:10.1007/s11030-009-9194-0
Yavari I, Nematpour M, Damghani T (2013) Sulfonoketenimides as key intermediates for the synthesis of 2-thioxo-2H-1,3-thiazines and 2-arylimino-2H-1,3-thiazines. Mol Divers 17:801–808. doi:10.1007/s11030-013-9478-2
Burnett MN, Johnson CK (1996) ORTEP-III report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA
Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr 64:112–122. doi:10.1107/S0108767307043930
Acheson RM, Foxtoand MW, Miller GR (1965) Addition reactions of heterocyclic compounds. Part XXIV. Adducts from thiaxoles, benxoxaxole, and 2-methylbenxoselenrtxole with dimethyl acetylenedicarboxylate. J Chem Soc 585:3200–3206. doi:10.1039/JR9650003200
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Yavari, I., Ghafouri, K., Zahedi, N. et al. A synthesis of functionalized arylthio-acrylates, benzo[b][1,4]thiazines and benzo[4,5]thiazolo[3,2-a]azepines from 2-methylbenzothiazole and acetylenic esters in aqueous media. Mol Divers 21, 527–532 (2017). https://doi.org/10.1007/s11030-017-9751-x
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11030-017-9751-x