Nazarov cyclization

What is Nazarov cyclization?

Nazarov cyclization is an organic chemical reaction in which a compound with a conjugated enone and a terminal alkene is converted into a cyclohexenone through the action of an acid catalyst. The reaction was discovered by the Russian chemist Pyotr Nazarov in the 1950s and is named after him..

Nazarov cyclization reaction
Nazarov cyclization

Nazarov cyclization typically proceeds through an intermediate called a “Nazarov intermediate,” which is a cyclic compound with a conjugated enone and a terminal alkene. The intermediate can then be hydrolyzed to produce the final cyclohexenone product..

One of the key features of the Nazarov cyclization is that it allows for the synthesis of cyclohexenones from compounds with a conjugated enone and a terminal alkene, which can be useful for synthesizing a wide range of compounds for various applications. Cyclohexenones are also important intermediates in a number of chemical reactions and can serve as starting materials for the synthesis of other compounds..

Nazarov cyclization can be performed under a variety of conditions, including both acidic and basic conditions. The choice of conditions depends on the specific reactants and desired product, and can be influenced by factors such as the stability of the intermediate and the ability to control the regiochemistry of the reaction..

Summary

Nazarov cyclization is a useful tool for synthesizing cyclohexenones and has a wide range of applications in the field of organic chemistry..

References

  • I. N. Nazarov, I. B. Torgov and L. N. Tcrckhova, Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1942, 200
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1943, 389
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1945, 65
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1946, 529
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1946, 633
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1947, 205
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1947, 277
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1947, 353
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1947, 495
  • I. N. Nazarov et al., Izv. Ahad. Nauk S.S.S.R., Otd. Khim. Nauk 1947, 647
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