SYNTHESIS OF POTENTIALLY BIOLOGICALLY ACTIVE SPYROHETEROCYCLIC COMPOUNDS VIA CARBOCYCLIC REFORMATSKY REAGENTS

Authors

  • N.F. Kirillov Perm State National Research University
  • Е.А. Nikiforova Perm State National Research University
  • D.V. Baybarodskikh Perm State National Research University
  • E.Yu. Zelina Perm State National Research University
  • R.R. Machmudov Perm State National Research University

DOI:

Keywords:

Reformatsky reagent, pyran-2-ones, pyperidine-2, 6-diones, pyran-2, 4-diones, furanones, furofurandiones, furopirroldiones, chromenones, chromenopyridintriones, azetidinones

Abstract

Synthesis of spyroheterocyclic products via the interaction of carbocyclic Reformatsky reagents with electrophilic substrates, such as carbonyl and carbonyl-containing compounds, α,β- unsaturated carbonyl compounds and amides, as well as anhydrides of dicarboxylic acids was studied during the research. Spyroheterocyclic structures are formed via cyclisation of intermediates, produced by addition of Reformatsky reagents to electrophiles.

Supporting Agencies
Работа выполнена при финансовой поддержке Российского фонда фундаментальных исследований (грант № 13-03-96010).

Author Biographies

  • N.F. Kirillov, Perm State National Research University
    кандидат химических наук, доцент кафедры органической химии
  • Е.А. Nikiforova, Perm State National Research University
    кандидат химических наук, старший преподаватель кафедры органической химии
  • D.V. Baybarodskikh, Perm State National Research University
    инженер
  • E.Yu. Zelina, Perm State National Research University
    инженер
  • R.R. Machmudov, Perm State National Research University
    кандидат фармацевтических наук, доцент кафедры экологии человека и безопасности жизнедеятельности

References

  1. Kirillov N.F., Slepukhin P.A., Nikiforova E.A., Vasyanin A.N., Shurov S.N., Kashkin P.M. Reaction of 1-(2- bromo-4-methoxy-1,4-dioxobutyl)-cyclohexanecarboxylate with zinc and aromatic aldehydes // Mendeleev Communications. - 2014. - Vol. 24. - No 3. - P. 178-179.
  2. Kirillov N.F., Zelina E.U., Nikiforova E.A. Vzaimodejstvie metil 1-bromciklogeksankarboksilata s cinkom i bis(N-arilmetilidengidrazidami) alifaticeskih dikarbonovyh kislot // Tret’a Vseros. nauc. konf. (s mezdunar. ucastiem) <>. - M.: RUDN, 2014. - S. 187.
  3. Komarova D.S., Kirillov N.F., Nikiforova E.A. Vzaimodejstvie metil 1-bromciklogeksankarboksilata s cinkom i aromaticeskimi al’degidami // Tam ze. - S. 192.
  4. Nikiforova E.A., Kirillov N.F., Bajbarodskih D.V. Vzaimodejstvie karbocikliceskih reaktivov Reformatskogo s ciklogeksilamidami 2-oksohromen-3-karbonovyh kislot // Tam ze. - S. 244.
  5. Kirillov N.F., Nikiforova E.A. Vzaimodejstvie metil 1-bromciklopentan- i 1-bromciklogeksankarboksilatov s cinkom i 2-arilmetilenindan-1,3-dionami // Zurn. org. himii. - 2014. - T. 50. - Vyp. 6. - S. 804-807.
  6. Kirillov N.F., Nikiforova E.A., Surov S.N. Vzaimodejstvie metil 1-bromciklopentankarboksilata s cinkom i amidami 3-aril-2-cianopropenovyh kislot // Tam ze. - S. 846-849.
  7. Kirillov N.F., Nikiforova E.A. Posledovatel’noe vzaimodejstvie metil (1-bromciklogeks-1- il)formiata s cinkom i nitrobenzal’degidami // Tam ze. - S. 923-924.
  8. Kirillov N.F., Melekhin V.S., Shurov S.N., Slepukhin P.A., Vasyanin A.N., Nikiforova E.A. Synthesis and structure of 4-aryl-6a-aryl-3,3:6,6-dipropanotetrahydro-2H-furo[3,2-b]pyrrole-2,5(3H)-diones // Mendeleev Communications. - 2014. - Vol. 24. - No 5. - P. 283-285.
  9. Kirillov N.F., Slepuhin P.A., Nikiforova E.A., Vasanin A.N., Surov S.N. Vzaimodejstvie metilovyh efirov 1-bromcikloalkankarbonovyh kislot s cinkom i benzoinom // Izv. AN. Ser. himiceskaa. - 2014. - No 6. - S. 1438-1440.
  10. Kirillov N.F., Slepuhin P.A., Nikiforova E.A. Stroenie 3,3:6,6-dibutano-3a-metil-6a- feniltetragidrofuro[3,2-b]furan-2,5-diona // Zurn. strukt. himii. - 2015. - T. 56. - No 1. - S. 193-194.
  11. Kirillov N.F., Mahmudov R.R., Nikiforova E.A., Mardanova L.G. Sintez i antinociceptivnaa aktivnost’ proizvodnyh 4-(1-metoksikarbonilciklogeksil)- i 6-brom-4-(1- metoksikarbonilciklogeksil)-2-oksohroman-3-karbonovyh kislot // HFZ. - 2015. - T. 49. - No 8. - S. 13-15.
  12. Kirillov N.F., Nikiforova E.A., Bajbarodskih D.V. Vzaimodejstvie metil 1-bromcikloalkankarboksilatov s cinkom i ciklogeksilamidami 2-oksohromen- i 6-brom-2- oksohromen-3-karbonovyh kislot // Zurn. org. himii. - 2015. - T. 51. - Vyp. 4. - S. 535-538.
  13. Kirillov N.F., Nikiforova E.A., Vasanin A.N., Dmitriev M.V. Sintez 16-aril-15- oksadispiro[5.1.5.3]geksadekan-7,14-dionov reakciej Reformatskogo // Tam ze. - S. 530-534.
  14. Kirillov N.F., Nikiforova E.A., Dmitriev M.V. Stroenie etil E-6-brom-4[1- (metoksikarbonil)ciklobutil]-2-oksohroman-3-karboksilata // Zurn. strukt. himii. - 2015. - T. 56. - No 7. - S. 1474-1476.
  15. Kaskin P.M. Sintez monometilovyh efirov oksodikarbonovyh kislot reakciej Reformatskogo / Sb. statej stud. konf. <>. - Perm’, 2014. - S. 102-103.
  16. Kirillov N.F., Nikiforova E.A., Mahmudov R.R., Mardanova L.G. Sposob polucenia 1-[3-(ciklogeksilkarbomoil)-2-oksohroman-4-il]ciklopentankarboksilata, proavlausego anal’geticeskuu aktivnost’ // Patent RF No 2549357. Opubl. 27.04.2015 g. Bul. No 12.
  17. Kirillov N.F., Nikiforova E.A., Mahmudov R.R., Mardanova L.G. Sposob polucenia metil 1-[(1,3-di- okso,2,3-digidro-1N-inden-2-il)(4-metilfenil)metil]ciklogeksankarboksilata, proavlausego anal’geticeskuu aktivnost’ // Patent RF No 2549566. Opubl. 27.04.2015 g. Bul. No 12.

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Published

2017-09-05

Issue

No. 2 (2017)

Section

Research: theory and experiment

How to Cite

Kirillov, N. ., Nikiforova Е. ., Baybarodskikh, D. ., Zelina, E. ., & Machmudov, R. . (2017). SYNTHESIS OF POTENTIALLY BIOLOGICALLY ACTIVE SPYROHETEROCYCLIC COMPOUNDS VIA CARBOCYCLIC REFORMATSKY REAGENTS. Perm Federal Research Centre Journal, 2, 54-60. https://journal.permsc.ru/index.php/pscj/article/view/PSCJ2017n2p7