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. 2025 Jun 9;15(24):19417-19420.
doi: 10.1039/d5ra03000e. eCollection 2025 Jun 4.

[4 + 2] Cycloaddition of α-bromotrifluoromethylhydrazone with alkenes: synthesis of trifluoromethyltetrahydropyridazines

Yanhui Zhao  1 , Hemin Rong  1 , Khurshed Bozorov  2 , Xueqing Zhang  1 , Buer Song  1 , Wei Liu  1
Affiliations

[4 + 2] Cycloaddition of α-bromotrifluoromethylhydrazone with alkenes: synthesis of trifluoromethyltetrahydropyridazines

Yanhui Zhao et al. RSC Adv. .

Abstract

A catalyst-free [4 + 2] cyclization process between trifluoromethyl-containing 1,2-diazabuta-1,3-diene and simple olefins was developed by in situ generation. Under mild conditions, trifluoromethyl-containing 1,4,5,6-tetrahydropyridazine compounds were obtained, in high yields (up to 96% yields).

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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Selected examples of α-bromoacylhydrazones participated cycloaddition reactions.
Scheme 2
Scheme 2. Substrate scope of hydrazonesa,b. aAll reactions were carried out by using 0.2 mmol of 1, 3 eq. of 2a and 2 eq. of Na2CO3 in 3 mL of CH2Cl2. bIsolated yields.
Scheme 3
Scheme 3. Substrate scope for simple alkenesa,b. aAll reactions were carried out by using 0.2 mmol of 1a, 3 eq. of 2 and 2 eq. of Na2CO3 in 3 mL of CH2Cl2. bIsolated yields.
Scheme 4
Scheme 4. Substrate scope for hydrazone 1m with substituted styrenesa,b. aAll reactions were carried out by using 0.2 mmol of 1m, 3 eq. of 2 and 2 eq. of Na2CO3 in 3 mL of CH2Cl2. bIsolated yields.
Scheme 5
Scheme 5. Proposed reaction mechanism.
See this image and copyright information in PMC

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