Skip to main content
Log in

Alternative Synthetic Routes to Dioxolanes and Thiadiazines

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The hydrolysis of 2-methylbut-3-yn-2-yl carbamate gave 4,4-dimethyl-5-methylidene-1,3-dioxo­lan-2-one, whereas 2-methylbut-3-yn-2-ol was converted under similar conditions to 3-hydroxy-3-methylbutan-2-one. 2-[2-Amino(hydrazinyl)-6H-1,3,4-thiadiazin-5-yl]propan-2-yl carbamates were synthesized by reacting 4-bromo-2-methyl-3-oxobutan-2-yl carbamate with thiosemicarbazide and carbonothioic dihydrazide, respectively.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme
Scheme
Fig. 1.
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Chang, L., Zhiani, R., and Sadeghzadeh, S.M., RSC Adv., 2019, vol. 9, p. 16955. https://doi.org/10.1039/c9ra02680k

    Article  CAS  Google Scholar 

  2. Glazunova, E.M., Glebova, N.V., Khaidarov, K.Kh., Lebe­deva, L.D., Avots, A.A., Akif’ev, O.N., and Pula­tov, A.M., USSR Inventor’s Certificate no. 1448440, 1987.

  3. Khaidarov, K.Kh., Sarkisyan, K.Kh., Sergienko, A.V., Ivashev, M.N., Kuyantseva, A.M., Lysenko, T.A., Arl’t, A.V., Zatsepina, E.E., and Savenko, I.A., Mezhdunar. Zh. Eksp. Obraz., 2013, no. 8, p. 101.

    Google Scholar 

  4. Scheibler, H. and Fischer, A., Ber., 1922, vol. 55, p. 2903. https://doi.org/10.1002/cber.19220550868

    Article  Google Scholar 

  5. Hennion, G.F. and Watson, E.J., J. Org. Chem., 1958, vol. 23, p. 656. https://doi.org/10.1021/jo01099a002

    Article  CAS  Google Scholar 

  6. Hennion, G.F. and Teach, E.G., J. Am. Chem. Soc., 1953, vol. 75, p. 4297. https://doi.org/10.1021/ja01113a044

    Article  CAS  Google Scholar 

  7. Yuan, Y., Xie, Y., Song, D., Zeng, Ch., Chaemchuen, S., Chen, Ch., and Verpoort, F., Appl. Organomet. Chem., 2017, vol. 31, article ID e3867. https://doi.org/10.1002/aoc.3867

  8. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scu­seria, G.E., Robb, M.A., Cheeseman, J.R., Montgo­mery, J.A., Jr., Vreven, T., Kudin, K.N., Burant, J.C., Millam, J.M., Iyengar, S.S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G.A., Naka­tsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J.E., Hratchian, H.P., Cross, J.B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Ayala, P.Y., Morokuma, K., Voth, G.A., Salvador, P., Dannenberg, J.J., Zakrzew­ski, V.G., Dapprich, S., Daniels, A.D., Strain, M.C., Farkas, O., Malick, D.K., Rabuck, A.D., Raghava­chari, K., Foresman, J.B., Ortiz, J.V., Cui, Q., Baboul, A.G., Clifford, S., Cios­lowski, J., Stefa­nov, B.B., Liu, G., Liashenko, A., Piskorz, P., Koma­romi, I., Martin, R.L., Fox, D.J., Keith, T., Al-Laham, M.A., Peng, C.Y., Nanayak­kara, A., Challa­combe, M., Gill, P.M.W., Johnson, B., Chen, W., Wong, M.W., Gonzalez, C., and Pople, J.A., Gaussian 03, Revision C.02, Wallingford CT: Gaussian, 2004.

  9. Isobaev, M.D., Glazunova, E.M., Glebova, N.V., and Khasanova, D.K., Zh. Org. Khim., 1989, vol. 25, p. 1184.

    CAS  Google Scholar 

  10. Chupakhin, O.N., Sidorova, L.P., Perova, N.M., Charushin, V.N., Rusinov, L.V., and Mulyar, A.G., RU Patent no. 2259371, 2005.

  11. Pulatov, E.Kh., Isobaev, M.D., and Mavlonov, B.G., Russ. Chem. Bull., Int. Ed., 2016, vol. 65, p. 2475. https://doi.org/10.1007/s11172-016-1609-3

    Article  CAS  Google Scholar 

  12. Pulatov, E.Kh., Isobaev, M.D., Mavlonov, B.G., and Abdullaev, T.Kh., Russ. Chem. Bull., Int. Ed., 2018, vol. 67, p. 1106. https://doi.org/10.1007/s11172-018-2188-2

    Article  CAS  Google Scholar 

  13. Nazarov, I.N., Burmistrova, M.S., and Akhrem, A.A., Zh. Obshch. Khim., 1959, vol. 29, p. 735.

    CAS  Google Scholar 

  14. Kroiß, S. and Steglich, W., Tetrahedron, 2004, vol. 60, p. 4921. https://doi.org/10.1016/j.tet.2004.03.092

    Article  CAS  Google Scholar 

Download references

Funding

This study was performed under financial support by the Ministry of Economy and Trade of Tajikistan Republic (project no. 0116 EO 00547).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to M. D. Isobaev.

Ethics declarations

The authors declare the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 3, pp. 391–399 https://doi.org/10.31857/S0514749221030071.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Isobaev, M.D., Pulatov, E.K., Abdullaev, T.K. et al. Alternative Synthetic Routes to Dioxolanes and Thiadiazines. Russ J Org Chem 57, 369–375 (2021). https://doi.org/10.1134/S1070428021030076

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021030076

Keywords:

Navigation