A [4+2] CYCLOADDITION OF PUSH-PULL STYRENES TO 1,2-NAPHTHOQUINONE 1-METHIDES: A SYNTHESIS OF 2-ARYL-2,3-DIHYDRO-1<i>H</i>-BENZO[<i>f</i>]CHROMENES

Authors

  • Kirill S. Korzhenko Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Anastasiya S. Yushkova Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Darya А. Rashchepkina Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Oleg P. Demidov North Caucasus Federal University, 1 Pushkina St., Stavropol 355009
  • Dmitry V. Osipov Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100
  • Vitaly А. Osyanin Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

Keywords:

2-aryl-2,3-dihydro-1H-benzo[f]chromenes, isoflavans, 2-naphthol Mannich bases, o-quinone methides, Cope reaction, Diels–Alder reaction, push-pull styrenes

Abstract

A regioselective and trans-diastereoselective method for the preparation of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes based on 2-naphthol Mannich bases as precursors of 1,2-naphthoquinone 1-methides and highly polarized β-(N,N-dimethylamino)styrene was developed. The resulting cycloadducts were transformed into cyclic acetals and hemiacetals as well as introduced into the Cope reaction leading to 2-aryl-1H-benzo[f]chromenes.

Author Biographies

Kirill S. Korzhenko, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

аспирант кафедры органической химии

Darya А. Rashchepkina, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

аспирант кафедры органической химии

Oleg P. Demidov, North Caucasus Federal University, 1 Pushkina St., Stavropol 355009

профессор

Dmitry V. Osipov, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

кандидат химических наук, доцент

Vitaly А. Osyanin, Samara State Technical University, 244 Molodogvardeyskaya St., Samara 443100

профессор кафедры орнанической химии

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Published

2024-01-10

Issue

Vol. 59 No. 11/12 (2023)

Section

Original Papers