A Convenient Preparation of Thieno[3,2-c]pyrazole^[1]

Abstract

A practical synthesis of multigram quantities of 1H-thi­eno[3,2-c]pyrazole is presented in which the Jacobson reaction serves as the key step.

Key words

aminations - cyclizations - polycycles - heterocycles

• References

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• 2 Current address: Retired.
• 3 Current address: Chemical Research, Sanofi US, 153 2nd Ave, Waltham, MA 02451, USA.
• 4 Current address: 33 Casale Drive South, Warren, NJ 07059, USA.
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For similar alane reductions, see also:
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• 19 An aliquot was removed and worked up by filtration, concentration of the filtrate, and chromatography of the residue. Combination and concentration of amide-containing fractions gave N-(2-methyl-3-thienyl)acetamide as a light-beige solid. ¹H NMR: δ = 2.18 (s, 3 H), 2.31 (s, 3 H), 7.01 (d, 1 H), 7.27 (d, 1 H). ¹³C NMR: δ = 12.25, 23.73, 120.69, 124.34, 126.10, 131.49, 167.84. Anal. Calcd for C₇H₉NOS: C, 54.17; H, 5.84; N, 8.78; S, 20.66. Found: C, 53.92; H, 5.86; N, 8.78; S, 20.51.
• 20 Although the Jacobson reaction has been shown to yield a mixture of N ¹-acetyl and N ²-acetyl tautomers, we never obtained any of the N ²-acetyl material.
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