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Synlett

Volumn , Issue 12, 2008, Pages 1817-1820

Reaction of 2-alkynylbenzoyl cyanides with carboxylic acids producing functionalized indenones

(2) Shimizu, Hiroshi a Murakami, Masahiro a

a KYOTO UNIVERSITY (Japan)

Author keywords

Benzoyl cyanides; Carboxylic acids; Cyclization; Heterocycles; Indenones

Indexed keywords

2 ALKYNYLBENZOYL CYANIDE DERIVATIVE; ALLENE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; INDENONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 48349131438 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078501 Document Type: Article

Times cited : (12)

References (26)

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4
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- For recent examples of attack of carbon nucleophiles to the carbonyl group, see: a
- For recent examples of attack of carbon nucleophiles to the carbonyl group, see: (a) Ikeda, Z.; Hirayama, T.; Matsubara, S. Angew. Chem. Int. Ed. 2006, 45, 8200.
- (2006) Angew. Chem. Int. Ed , vol.45 , pp. 8200
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- (f) Wiles, C.; Watts, P.; Haswell, S. J.; Pombo-Villar, E. Chem. Commun. 2002, 1034.
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- Wiles, C.¹ Watts, P.² Haswell, S.J.³ Pombo-Villar, E.⁴

10
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11
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12
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13
- 48349089893
- Representative Procedure for the Preparation of 2-Alkynylbenzoyl Cyanide 2 Oxalyl chloride (1.60 mL, 18.7 mmol) was added dropwise to a mixture of 2-(1-hexyn-1-yl) benzoic acid (1a, 3.43 g, 17.0 mmol) and DMF (2 drops) in CH2Cl2 (35 mL, The reaction mixture was stirred for 1.5 h at r.t. Then, volatile components were removed in vacuo to give crude acid chloride. A solution of the crude acid chloride in MeCN (20 mL) was added to a stirred suspension of CuCN (3.00 g, 33.5 mmol) in MeCN (20 mL) at r.t. After the mixture was stirred for 1 h at 70°C, the resulting clear solution was cooled to r.t. and concentrated in vacuo. The residue was washed with Et2O, filtrated and concentrated in vacuo again. The residue was purified rapidly by silica gel column chromatography (hexane and then hexane-Et2O, 50:1) to afford 2-(1-hexyn-1-yl)benzoyl cyanide (2a, 2.83 g, 79, 1H NMR 300 MHz, CDCl3, δ, 0
- +]: 211.0997; found: 211.0997. Compounds 2b-e were prepared by a similar procedure.

14
- 0002655566
- Normant, J. F.; Piechucky, C. Bull. Soc. Chem. Fr. 1972, 6, 2402.
- (1972) Bull. Soc. Chem. Fr , vol.6 , pp. 2402
- Normant, J.F.¹ Piechucky, C.²

15
- 48349088893
- No reaction occurred at room temperature
- No reaction occurred at room temperature.

16
- 48349087432
- Representative Procedure for the Cyclization Reaction of 2 with 4 A mixture of 2-(1-hexyn-1-yl)benzoyl cyanide (2a, 42.3 mg, 0.20 mmol) and benzoic acid (4a, 48.8 mg, 0.40 mmol) in p-xylene (1.0 mL) was stirred at 140°C for 24 h under an argon atmosphere, and then the solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (toluene-EtOAc, 10:1) to afford 2-benzoylamino-3- pentanoylindenone 5aa (55.9 mg, 84, 1H NMR (300 MHz, CDCl3, δ, 0.91 (3 H, t, J, 7.2 Hz, 1.38 (2 H, pseudo sext, J, 7.5 Hz, 1.74 (2 H, pseudo quin, J, 7.5 Hz, 2.75 (2 H, t, J, 7.5 Hz, 7.14 (2 H, t, J, 7.5 Hz, 7.35 (1 H, dt, J, 1.2, 7.5 Hz, 7.44-7.56 (3 H, m, 7.56-7.64 (1 H, m, 7.87-7.94 (2 H, m, 8.40 (1 H, br s, 13C NMR 75 MHz, CDCl3, δ, 14.1, 22.6, 25.8, 44.1, 121.9, 124.4, 126.8, 127.3, 127.6, 127.9, 129.1, 132.5, 132
- +]: 333.1365; found: 333.1361.

17
- 48349091589
- 4-catalyzed reaction of acid chloride with TMSCN: Olah, G. A.; Arvanaghi, M.; Prakash, G. K. S. Synthesis 1983, 636.
- 4-catalyzed reaction of acid chloride with TMSCN: Olah, G. A.; Arvanaghi, M.; Prakash, G. K. S. Synthesis 1983, 636.

18
- 48349098123
- When 5ai was exposed to same reaction conditions, a deuterium was incorporated only in 17% at the α-position of the carbonyl group.
- When 5ai was exposed to same reaction conditions, a deuterium was incorporated only in 17% at the α-position of the carbonyl group.

19
- 48349111566
- No reaction occurred with secondary amines such as a piperidine and N-benzylmethylamine.
- No reaction occurred with secondary amines such as a piperidine and N-benzylmethylamine.

20
- 0001120030
- For cyclocondensation of β-enamino carbonyl compounds with amidines and hydrazines, see: a
- For cyclocondensation of β-enamino carbonyl compounds with amidines and hydrazines, see: (a) Bredereck, H.; Sell, R.; Effenberger, F. Chem. Ber. 1964, 97, 3407.
- (1964) Chem. Ber , vol.97 , pp. 3407
- Bredereck, H.¹ Sell, R.² Effenberger, F.³

21
- 0023029690
- (b) Kvita, V. Synthesis 1986, 786.
- (1986) Synthesis , pp. 786
- Kvita, V.¹

22
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- (c) Bredereck, H.; Herlinger, H.; Schweizer, E. Chem. Ber. 1960, 93, 1208.
- (1960) Chem. Ber , vol.93 , pp. 1208
- Bredereck, H.¹ Herlinger, H.² Schweizer, E.³

23
- 0003783634
- (d) Plath, P.; Rohr, W. Synthesis 1982, 318.
- (1982) Synthesis , pp. 318
- Plath, P.¹ Rohr, W.²

24
- 48349124250
- Representative Procedure for the Synthesis of Indenopyrimidine A mixture of 5ai (27.2 mg, 0.10 mmol) and benzamidine hydrochloride (8a, 38.5 mg, 0.20 mmol) in pyridine (1.0 mL) was stirred at 100°C for 24 h under an argon atmosphere, and then the reaction mixture was cooled and diluted with EtOAc (5 mL) and H2O (5 mL, The organic layer was separated and the aqueous layer was extracted with EtOAc (3 x 3 mL, The combined extracts were washed with H2O and brine, and dried over MgSO4. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (toluene-EtOAc, 20:1) to afford 4-butyl-2-phenyl-9H-indeno[2,1-d]pyrimidin-9-one (9aia, 28.1 mg, 89, 1H NMR (300 MHz, CDCl3, δ, 1.04 (3 H, t, J, 7.5 Hz, 1.45-1.65 (2 H, m, 1.92 (2 H, quin, J, 7.7 Hz, 3.13 (2 H, t, J, 7.5 Hz, 7.33-7.47 (1 H, m, 7.47-7.57 3 H, m, 7.57
- +]: 314.1419; found: 314.1422.

25
- 48349094710
- Representative Procedure for the Synthesis of Indenopyrazole To a stirred solution of 5ai (27.2 mg, 0.10 mmol) in 1,4-dioxane (0.5 mL) under an argon atmosphere was added a solution of methylhydrazine (5.5 mg, 0.12 mmol) in 1,4-dioxane (0.5 mL) at 60°C over 5 min. After being stirred for 3 h, the reaction mixture was cooled and diluted with EtOAc (5 mL) and H 2O (5 mL, The organic layer was separated and the aqueous layer was extracted with EtOAc (4 x 3 mL, The combined extracts were washed with H 2O and brine, and dried over MgSO4. The solvent was evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (CHCl3-EtOAc, 10:1) to afford 3-butyl-2-methyl-8H- indeno[2,1-c]pyrazol-8-one (12ai, 12.4 mg, 52, 1H NMR (300 MHz, CDCl3, δ, 0.97 (3 H, t, J, 7.3 Hz, 1.39-1.49 (2 H, m, 1.63-1.73 (2 H, m, 2.74 (2 H, t, J, 7.5 Hz, 3.83 3
- +]: 240.1263; found: 240.1260. The position of the methyl group was identified by NOE measurement.

26
- 33746868887
- For selective formation of N-substituted pyrazoles from N-methoxy-N-methyl-β-enaminoketoesters, see: Persson, T.; Nielsen, J. Org. Lett. 2006, 8, 3219.
- For selective formation of N-substituted pyrazoles from N-methoxy-N-methyl-β-enaminoketoesters, see: Persson, T.; Nielsen, J. Org. Lett. 2006, 8, 3219.

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