Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones

Lee J. Silverberg; Carlos Pacheco; Anthony Lagalante; John Tierney; Joshua T. Bachert; J. Austin Bayliff; Ryan V. Bendinsky; Aaron S. Cali; Liuxi Chen; Avril D. Cooper; Michael J. Minehan; Caitlin R. Mroz; Duncan J. Noble; Alexander K. Weisbeck; Yiwen Xie; Ziwei Yang

doi:10.24820/ark.5550190.p009.875

Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones

Lee J. Silverberg, Carlos Pacheco, Anthony Lagalante, John Tierney, Joshua T. Bachert, J. Austin Bayliff, Ryan V. Bendinsky, Aaron S. Cali, Liuxi Chen, Avril D. Cooper, Michael J. Minehan, Caitlin R. Mroz, Duncan J. Noble, Alexander K. Weisbeck, Yiwen Xie, Ziwei Yang

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

1 Scopus citations

Abstract

A series of thirteen novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of N-phenyl-C-aryl imines with thiosalicylic acid. The spectroscopic and physical properties are reported and discussed. ¹H-¹⁹F and ¹³C-¹⁹F couplings were observed in the NMR spectra of fluorinated compounds. Through-space interactions were observed in the ¹H and ¹³C NMR spectra of the ortho-nitro compound. Trends were observed in the IR and UV absorptions of the ortho/meta/para-nitro series.

Original language	English (US)
Pages (from-to)	122-143
Number of pages	22
Journal	Arkivoc
Volume	2016
Issue number	6
DOIs	https://doi.org/10.24820/ark.5550190.p009.875
State	Published - 2016

All Science Journal Classification (ASJC) codes

Organic Chemistry

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Silverberg, L. J., Pacheco, C., Lagalante, A., Tierney, J., Bachert, J. T., Bayliff, J. A., Bendinsky, R. V., Cali, A. S., Chen, L., Cooper, A. D., Minehan, M. J., Mroz, C. R., Noble, D. J., Weisbeck, A. K., Xie, Y., & Yang, Z. (2016). Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones. Arkivoc, 2016(6), 122-143. https://doi.org/10.24820/ark.5550190.p009.875

Silverberg, Lee J. ; Pacheco, Carlos ; Lagalante, Anthony ; Tierney, John ; Bachert, Joshua T. ; Bayliff, J. Austin ; Bendinsky, Ryan V. ; Cali, Aaron S. ; Chen, Liuxi ; Cooper, Avril D. ; Minehan, Michael J. ; Mroz, Caitlin R. ; Noble, Duncan J. ; Weisbeck, Alexander K. ; Xie, Yiwen ; Yang, Ziwei. / Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones. In: Arkivoc. 2016 ; Vol. 2016, No. 6. pp. 122-143.

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title = "Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones",

abstract = "A series of thirteen novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of N-phenyl-C-aryl imines with thiosalicylic acid. The spectroscopic and physical properties are reported and discussed. 1H-19F and 13C-19F couplings were observed in the NMR spectra of fluorinated compounds. Through-space interactions were observed in the 1H and 13C NMR spectra of the ortho-nitro compound. Trends were observed in the IR and UV absorptions of the ortho/meta/para-nitro series.",

author = "Silverberg, {Lee J.} and Carlos Pacheco and Anthony Lagalante and John Tierney and Bachert, {Joshua T.} and Bayliff, {J. Austin} and Bendinsky, {Ryan V.} and Cali, {Aaron S.} and Liuxi Chen and Cooper, {Avril D.} and Minehan, {Michael J.} and Mroz, {Caitlin R.} and Noble, {Duncan J.} and Weisbeck, {Alexander K.} and Yiwen Xie and Ziwei Yang",

year = "2016",

doi = "10.24820/ark.5550190.p009.875",

language = "English (US)",

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Silverberg, LJ, Pacheco, C, Lagalante, A, Tierney, J, Bachert, JT, Bayliff, JA, Bendinsky, RV, Cali, AS, Chen, L, Cooper, AD, Minehan, MJ, Mroz, CR, Noble, DJ, Weisbeck, AK, Xie, Y & Yang, Z 2016, 'Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones', Arkivoc, vol. 2016, no. 6, pp. 122-143. https://doi.org/10.24820/ark.5550190.p009.875

Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones. / Silverberg, Lee J.; Pacheco, Carlos; Lagalante, Anthony; Tierney, John; Bachert, Joshua T.; Bayliff, J. Austin; Bendinsky, Ryan V.; Cali, Aaron S.; Chen, Liuxi; Cooper, Avril D.; Minehan, Michael J.; Mroz, Caitlin R.; Noble, Duncan J.; Weisbeck, Alexander K.; Xie, Yiwen; Yang, Ziwei.

In: Arkivoc, Vol. 2016, No. 6, 2016, p. 122-143.

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

TY - JOUR

T1 - Synthesis and spectroscopic properties of a series of novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones

AU - Silverberg, Lee J.

AU - Pacheco, Carlos

AU - Lagalante, Anthony

AU - Tierney, John

AU - Bachert, Joshua T.

AU - Bayliff, J. Austin

AU - Bendinsky, Ryan V.

AU - Cali, Aaron S.

AU - Chen, Liuxi

AU - Cooper, Avril D.

AU - Minehan, Michael J.

AU - Mroz, Caitlin R.

AU - Noble, Duncan J.

AU - Weisbeck, Alexander K.

AU - Xie, Yiwen

AU - Yang, Ziwei

PY - 2016

Y1 - 2016

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AB - A series of thirteen novel 2-aryl-3-phenyl-2,3-dihydro-4H-1,3-benzothiazin-4-ones was prepared at room temperature by T3P-mediated cyclization of N-phenyl-C-aryl imines with thiosalicylic acid. The spectroscopic and physical properties are reported and discussed. 1H-19F and 13C-19F couplings were observed in the NMR spectra of fluorinated compounds. Through-space interactions were observed in the 1H and 13C NMR spectra of the ortho-nitro compound. Trends were observed in the IR and UV absorptions of the ortho/meta/para-nitro series.

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