Abstract
Pyrazino[2′,3′:4,5]thieno[3,2-d ]pyrimidine derivatives 6 were synthesized by the intermolecular aza-Wittig reaction of N -heteroaryl phosphazene derivatives with carboxylic acid chlorides. The heterocyclization occurs via imidoyl chloride intermediates derived from phosphazenes 4a ,b , obtained in a one-step process from α-azidothieno[2,3-b ]pyrazine carboxylic acid 3 . Moreover, cyclic pyrazinothienopyrimidines were prepared, in a two-step procedure, from amides and azidothienopyrazine-α-carbonyl chloride using an intramolecular aza-Wittig heterocyclization reaction strategy.
Key words
heterocycles - Wittig reaction - nitrogen - azides - cyclizations
References
For recent contributions, see:
1a
Cushman M.
Sambaiah T.
Jin G.
Illarionov B.
Fischer M.
Bacher A.
J. Org. Chem.
2004,
69:
601
1b
Haraguchi K.
Kubota Y.
Tanaka H.
J. Org. Chem.
2004,
69:
1831
1c
Depecker G.
Patino N.
Giorgio CD.
Terreux R.
Cabrol-Bass D.
Bailly C.
Aubertin A.-M.
Condom R.
Org. Biomol. Chem.
2004,
2:
74
For reviews on the synthesis and biological activity of thienopyridines, see:
2a
Litvinov VP.
Dotsenko VV.
Krivokolysko SG.
Russ. Chem. Bull. Int. Ed.
2005,
54:
864
2b
Bakhite EA.-G.
Phosphorus, Sulfur, Silicon Relat. Elem.
2003,
178:
929
3a
Chambhare RV.
Khadse BG.
Bobde AS.
Bahekar RH.
Eur. J. Med. Chem.
2003,
38:
89
3b Walter H. inventors; WO Patent 9914202.
; Chem. Abstr.
1999 , 130 , 252368
4a
Sishoo CJ.
Shirsath VS.
Rathod IS.
Yande VD.
Eur. J. Med. Chem.
2000,
35:
351
4b
Santagati M.
Modica M.
Santagati A.
Russo F.
Spampinato S.
Pharmazie
1996,
51:
7
5a
Quintela JM.
Peinador C.
González L.
Devesa I.
Ferrándiz ML.
Alcaraz MJ.
Riguera R.
Biorg. Med. Chem.
2003,
11:
863
5b
Quintela JM.
Peinador C.
González L.
Iglesias R.
Paramá A.
Alvarez F.
Sanmartín M.
Riguera R.
Eur. J. Med. Chem.
2003,
38:
265
5c
Rioja I.
Ubeda A.
Terencio MC.
Guillén I.
Riguera R.
Quintela JM.
Peinador C.
González L.
Alcaraz MJ.
Eur. J. Pharmacol.
2000,
397:
207
5d
Quintela JM.
Peinador C.
González LM.
Rioja I.
Terencio MC.
Ubeda A.
Alcaraz MJ.
Riguera R.
J. Med. Chem.
1999,
42:
4720
5e
Quintela JM.
Peinador C.
Veiga C.
González L.
Botana LM.
Alfonso A.
Riguera R.
Bioorg. Med. Chem.
1998,
6:
1911
5f
Quintela JM.
Peinador C.
Veiga MC.
Botana LM.
Alfonso A.
Riguera R.
Eur. J. Med. Chem.
1998,
33:
887
5g
Peinador C.
Ojea V.
Quintela JM.
J. Heterocycl. Chem.
1992,
29:
1693
6a
Chill L.
Aknin M.
Kashman Y.
Org. Lett.
2003,
5:
2433
6b
Pettit GR.
Tan R.
Xu J.
Ichihara Y.
Williams MD.
Boyd MR.
J. Nat. Prod.
1998,
61:
995
6c
Immamura N.
Nishijima M.
Takadera T.
Adachi K.
Sakai M.
Sano H.
J. Antibiot.
1997,
50:
8
7a
Baker DC.
Hand ES.
Plowman J.
Rampal JB.
Safavy A.
Haugwitz RD.
Narayanan VL.
Anticancer Drug Des.
1987,
2:
297
7b For a recent review, see: Pawar VG.
De Borggraeve WH.
Synthesis
2006,
2799
8 Burns CJ, Wilks AF, and Bu X. inventors; WO Patent 2005054230. For a recent example, see:
; Chem. Abstr . 2005 , 143, 60004
For reviews, see:
9a
Palacios F.
Alonso C.
Aparicio D.
Rubiales G.
de los Santos JM.
Tetrahedron
2007,
63:
523
9b
Palacios F.
Aparicio D.
Rubiales G.
Alonso C.
de los Santos JM.
Curr. Org. Chem.
2006,
10:
2371
9c
Eguchi S.
Top. Heterocycl. Chem.
2006,
6:
113
9d
Eguchi S.
ARKIVOC
2005,
(ii):
98
9e
Arqués A.
Molina P.
Curr. Org. Chem.
2004,
8:
827
9f
Fresneda PM.
Molina P.
Synlett
2004,
1
10a
Blanco G.
Quintela JM.
Peinador C.
Tetrahedron
2007,
63:
2034
10b
Blanco G.
Seguí N.
Quintela JM.
Peinador C.
Chas M.
Toba R.
Tetrahedron
2006,
62:
11124
10c
Vázquez D.
Peinador C.
Quintela JM.
Tetrahedron
2004,
60:
275
10d
Álvarez-Sarandés R.
Peinador C.
Quintela JM.
Tetrahedron
2001,
57:
5413
11
Okawa T.
Toda M.
Eguchi S.
Kakehi A.
Synthesis
1998,
1467
12
Molina P.
Conesa C.
Velasco MD.
Liebigs Ann./Recl.
1997,
107
13
Wamhoff H.
Hermann S.
Stölben S.
Nieger M.
Tetrahedron
1993,
49:
581
14
Ding M.-W.
Huang N.-Y.
He H.-W.
Synthesis
2005,
1601
15
Zbiral E.
Bauer E.
Stroh J.
Monatsh. Chem.
1971,
102:
168
16
Lowe-Ma CK.
Nissan RA.
Wilson WS.
J. Org. Chem.
1990,
55:
3755
17 Crystallographic data (excluding structure factors) for 6b and 9a have been deposited with the Cambridge Crystallographic Data Center as supplementary publication numbers 6b : CCDC 668435, and 9a : CCDC 668436. Copies of the data may be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44 1223 33603 or e-mail: deposit@ccdc.cam.ac.uk).
18
Sheldrick GM.
SHELXL-97 Program
University of Göttingen;
Germany:
1997.