Article · Wikipedia archive · Last revised Jul 10, 2026

Bradsher cycloaddition

The Bradsher cycloaddition reaction, also known as the Bradsher cyclization reaction is a form of the Diels–Alder reaction which involves the [4+2] addition of a common dienophile with a cationic aromatic azadiene such as acridizinium or isoquinolinium.

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Bradsher [4+2] cycloaddition between pyrido[1,2-b]isoquinolin-5-ium and maleic anhydride in acetic acid, yielding the Diels-Alder adduct (6S,11R,12R,16R)-13,15-dioxo-6,11-dihydro-6,11-[3,4]furanopyrido[1,2-b]isoquinolin-5-ium. source ↗

The Bradsher cycloaddition reaction, also known as the Bradsher cyclization reaction is a form of the Diels–Alder reaction which involves the [4+2] addition of a common dienophile with a cationic aromatic azadiene such as acridizinium or isoquinolinium.

The Bradsher cycloaddition was first reported by C. K. Bradsher and T. W. G. Solomons in 1958.123

References

References

  1. C. K. Bradsher, T. W. G. Solomons (1958). "Acridizinium Ion Chemistry. II.1The Diels-Alder Reaction". J. Am. Chem. Soc. 80 (4): 933. Bibcode:1958JAChS..80..933B. doi:10.1021/ja01537a045.
  2. Merck Index, 14th Ed.
  3. C. K. Bradsher, J. A. Stone (1968). "Nature of the addition of dienophiles to the acridizinium ion". Journal of Organic Chemistry. 33 (2): 519. doi:10.1021/jo01266a009.