Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact:

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

Paper | Regular issue | Vol 96, No. 4, 2018, pp.664-676
Published online, 23rd March, 2018
DOI: 10.3987/COM-17-13861
Synthesis of Novel Angular and Linear Fused [5-6-5] Heterocycles by the Reaction of Methyl Cyano-(3-cyano-4,5-dihydro-2(3H)-furanylidene)acetate with Hydrazines and Dimethylformamide Dimethyl Acetal

Fumi Okabe-Nakahara,* Eiichi Masumoto, Hiroshi Maruoka, and Kenji Yamagata

*Faculty of Pharmaceutical Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


A convenient and efficient method for the synthesis of novel angular and linear fused [5-6-5] three heterocycles is described. Methyl cyano- (3-cyano-4,5-dihydro-2(3H)-furanylidene)acetate (1) was reacted with an excess of hydrazine monohydrate to give 3,4’-bipyrazole 5. Compound 5 was condensed with N,N-dimethylformamide dimethyl acetal (DMFDMA) to yield angular dipyrazolopyrimidine 6. On the other hand, pyrazoles 3b-d were obtained by reaction of 1 with hydrazines. Compounds 3b-d were reacted with hydrazine monohydrate, pyrazolopyridines 7a-c were taken. Compounds 7a-c were condensed with DMFDMA to give linear pyrazolotriazolopyridines 8a-c.