A quick synthesis of 1-arylpyrrolopyrazinones from linear alkynylamide derivatives

Synthesis

Volumn , Issue 6, 2010, Pages 971-978

  Pardo, Leticia M ^a   Tellitu, Imanol ^a   Domínguez, Esther ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Alkynylamides; Bicyclic compounds; Hypervalent iodine; Pyrazinones; Reductive aminations

Indexed keywords

BICYCLIC COMPOUNDS; CARBONYL GROUPS; FREE AMINO GROUPS; HETEROCYCLIZATIONS; HYPERVALENT IODINE; PROTECTING GROUP; PYRROLOPYRAZINONE; RAPID SYNTHESIS; REACTION CONDITIONS; TRIPLE BONDS;

AMIDES; AMINATION; BENZENE; CYCLIZATION; INDUSTRIAL CHEMICALS; IODINE; IODINE COMPOUNDS; SYNTHESIS (CHEMICAL);

COMPLEXATION;

1 (2 THIENYL) 3,4,7,8 TETRAHYDROPYRROLO[1,2 A]PYRAZIN 6(2H)ONE; 1 (4 CHLOROPHENYL) 3,4,7,8 TETRAHYDROPYRROLO[1,2 A]PYRAZIN 6(2H)ONE; 1 (4 CHLOROPHENYL)HEXAHYDROPYRROLO[1,2 A] PYRAZIN 6(2H)ONE; 1 (4 METHOXYPHENYL) 3,4,7,8 TETRAHYDROPYRROLO[1,2 A]PYRAZIN ONE; 1 (4 METHOXYPHENYL)HEXAHYDROPYRROLO[1,2 A]PYRAZIN 6(2H)ONE; 1 PHENYL 3,4,7,8 TETRAHYDROPYRROLO[1,2 A]PYRAZIN 6(2H)ONE; 1 PHENYLHEXAHYDROPYRROLO[1,2 A]PYRAZIN 6(2H)ONE; 5 BENZOYL N [2 (BENZYLOXYCARBONYLAMINO)ETHYL]PYRROLIDIN 2 ONE; 5 BENZOYL N [2 (TERT BUTOXYCARBONYLAMINO)ETHYL]PYRROLIDIN 2 ONE; [BIS(TRIFLUOROACETOXY)IODO]BENZENE; BENZENE; N [2 (BENZYLOXYCARBONYLAMINO)ETHYL] 5 (2 THIENYLCARBONYL)PYRROLIDIN 2 ONE; N [2 (BENZYLOXYCARBONYLAMINO)ETHYL] 5 (3 THIENYLCARBONYL)PYRROLIDIN 2 ONE; N [2 (BENZYLOXYCARBONYLAMINO)ETHYL] 5 (4 CHLOROBENZOYL)PYRROLIDIN 2 ONE; N [2 (BENZYLOXYCARBONYLAMINO)ETHYL] 5 (4 METHOXYBENZOYL)PYRROLIDIN 2 ONE; N [2 (TERT BUTOXYCARBONYLAMINO)ETHYL] 5 (2 THIENYLCARBONYL)PYRROLIDIN 2 ONE; N [2 (TERT BUTOXYCARBONYLAMINO)ETHYL] 5 (4 CHLOROBENZOYL)PYRROLIDIN 2 ONE; N [2 (TERT BUTOXYCARBONYLAMINO)ETHYL] 5 (4 METHOXYBENZOYL)PYRROLIDIN 2 ONE; PYRAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS;

EID: 77749328056     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1219218     Document Type: Article

References (12)

1. For a review on pharmacological properties and clinical uses of piracetam, see:, Winblad B, CNS Drug Rev. 2005 11 169
2. Pramiracetam (C) has shown improved efficacy in patients with senile or presenile cognitive impairment. See:, Manetti D, Ghelardini C, Bartolini A, Bellucci C, Dei S, Galeotti N, Gualtieri F, Romanelli M N., Scapecchi S, Teodori E, J. Med. Chem. 2000 43 1969
3. Nefiracetam (D) has been shown to modulate receptor systems such as the cholinergic and/or glutamatergic ones. See:, Moriguchi S, Shioda N, Maejima H, Zhao X, Marszalec W, Yeh J Z., Fukunaga K, Narahashi T, Mol. Pharmacol. 2007 71 580, Zhao X, Kuryatov A, Lindstrom J M., Yeh J Z., Narahashi T, Mol. Pharmacol. 2001 59 674
4. Martini E, Ghelardini C, Bertucci C, Dei S, Gualtieri F, Guandalini L, Manetti D, Scapecchi S, Teodori E, Romanelli M N., Med. Chem. 2005 1 473 See also ref. 2.
5. Farina C, Gagliardi S, Ghelardini C, Martinelli M, Norcini M, Parini C, Petrillo P, Ronzoni S, Bioorg. Med. Chem. 2008 16 3224, Pinza M, Farina C, Cerri A, Pfeiffer U, Riccaboni M T., Banfi S, Biagetti R, Pozzi O, Magnani M, Dorigotti L, J. Med. Chem. 1993 36 4214
6. Tellitu I, Serna S, Herrero M T., Moreno I, Domínguez E, SanMartin R, J. Org. Chem. 2007 72 1526, Serna S, Tellitu I, Domínguez E, Moreno I, SanMartin R, Org. Lett. 2005 7 3073
7. The pyrrolopyrazinone (1,4-diazabicyclo[4.3.0]nonane) skeleton has also been identified as the bicyclic constituent of the recently isolated natural product tunicyclin A. See:, Tian J.-M, Shen Y.-H, Yang X.-W, Liang S, Tang J, Shan L, Zhang W.-D, Org. Lett. 2009 11 1131 See also:, Macías A, Alonso E, DelPozo C, González J, Tetrahedron Lett. 2004 45 4657
8. For the synthetic and spectroscopic details of monoprotected diamines 1a, b, see, respectively:, Guy J, Caron K, Dufresne S, Michnick S W., Skene W G., Keillor J W., J. Am. Chem. Soc. 2007 129 11969, Krivickas S J., Tamanini E, Todd M H., Watkinson M, J. Org. Chem. 2007 72 8280
9. For some recent reviews on the Sonogashira reaction, see:, Heravi M M., Sadjadi S, Tetrahedron 2009 65 7761, Chinchilla R, Nájera C, Chem. Rev. 2007 107 874, Doucet H, Hierso J C., Angew. Chem. Int. Ed. 2007 46 834
10. These results led us to propose a mechanism in which the activated triple bond easily coordinates with the iodine(III) reagent and, hence, assisting the nucleophilic attack of the amidic nitrogen. In addition, alkyl-substituted alkynes also failed in the PIFA-mediated cyclization step
11. For recent books or reviews concerning the chemistry of the hypervalent iodine reagents, see:, Varvoglis A, The Organic Chemistry of Polycoordinated Iodine Wiley-VCH New York 1992, Varvoglis A, Hypervalent Iodine in Organic Synthesis Academic Press London 1997 Hypervalent Iodine Chemistry, Wirth T, Springer Berlin 2003, Togo H, Katoghi M, Synlett 2001 566, Togo H, Sakurani M, Synlett 2002 1966, Zhdankin V V., Stang P J., Chem. Rev. 2002 102 2523, Dauban P, Dodd R H., Synlett 2003 11, Stang P J., J. Org. Chem. 2003 68 2997, Wirth T, Angew. Chem. Int. Ed. 2005 44 3656, Richardson R D., Wirth T, Angew. Chem. Int. Ed. 2006 45 4402, Ciufolini M A., Braun N A., Canesi S, Ousmer M, Chang J, Chai D, Synthesis 2007 3759, Quideau S, Pouységu L, Deffieux D, Synlett 2008 467, Zhdankin V V., Stang P J., Chem. Rev. 2008 108 5299, Zhdankin V V., ARKIVOC 2009 (i) 1
12. For previous alternative approaches to the synthesis of this skeleton, see:, Scapecchi S, Martini E, Manetti D, Ghelardini C, Martelli C, Dei S, Galeotti N, Guandalini L, Romanelli M N., Teodori E, Bioorg. Med. Chem. 2004 12 71, Godet T, Bonvin Y, Vicent G, Merle D, Thozet A, Ciufolini M A., Org. Lett. 2004 6 3281, Hulme C, Ma L, Cherrier M P., Romano J J., Morton G, Duquenne C, Salvino J, Labaudiniere R, Tetrahedron Lett. 2000 41 1883, Martín- Martínez M, Ballaz S, Latorre M, Herranz R, García-López M T., Cenarruzabeitia E, DelRío J, González-Muñiz R, Chem. Pharm. Bull. 1998 46 782, Roth E, Altman J, Kapon M, Ben-Ishai D, Tetrahedron 1995 51 801 See also ref. 2.