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DOI: 10.1055/s-2007-983713
Synthesis of Masked 2-Amino-4,5-dihydro-4-oxopyrrole-3-carboxaldehydes
Publikationsverlauf
Publikationsdatum:
08. Juni 2007 (online)
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Abstract
2-(1-Substituted-2-amino-4,5-dihydro-4-oxopyrrol-3-yl)-1,3-dimethylbenzimidazolium and -3-methylbenzothiazolium chlorides were prepared by reaction of 2-(2,3-dihydro-1,3-dimethylbenzimidazol-2-ylidene)- and 2-(3-methylbenzothiazol-2-ylidene)-4-chloro-3-oxobutanenitriles with primary amines. The salts obtained were reduced to 4-(2,3-dihydro-1,3-dimethylbenzimidazol-2-yl)- and 4-(2,3-dihydro-3-methylbenzothiazol-2-yl)-1-substituted-5-aminopyrrol-3(2H)-ones. These pyrrole derivatives were shown to serve as synthetic equivalents of the corresponding 2-aminopyrrole-3-carboxaldehydes. Thus, their treatment with phenylhydrazine yielded 1-substituted 2-amino-4,5-dihydro-4-oxopyrrole-3-carboxaldehyde phenylhydrazones, whereas condensation with malonodinitrile afforded 1-substituted 6-amino-2,3-dihydro-3-oxopyrrolo[2,3-b]pyridine-5-carbonitriles.
Key words
amino aldehydes - heterocycles - nitriles - pyrroles - reductions
- 1 For a review, see:
Caluwe P. Tetrahedron 1980, 36: 2359 - 2
Eger K.Pfahl JG.Folkers G.Roth HJ. J. Heterocycl. Chem. 1987, 24: 425 -
3a
Abd El-Nabi HA. Tetrahedron 2000, 56: 3013 -
3b
Zaytsev AV.Anderson RJ.Meth-Cohn O.Groundwater PW. Tetrahedron 2005, 61: 5831 -
3c
Abd El-Nabi HA. J. Chem. Res., Synop. 2004, 5: 325 -
4a
Craig JC.Ekwuribe NN.Fu CC.Walker KAM. Synthesis 1981, 303 -
4b
Chikashita H.Ikegami S.Okumura T.Itoh K. Synthesis 1986, 375 -
4c
Chikashita H.Ishibaba M.Ori K.Itoh K. Bull. Chem. Soc. Jpn. 1988, 61: 3637 -
4d
Corey EJ.Boger DL. Tetrahedron Lett. 1978, 5 -
4e
Corey EJ.Boger DL. Tetrahedron Lett. 1978, 9 -
4f
Corey EJ.Boger DL. Tetrahedron Lett. 1978, 13 -
4g
Chikashita H.Itoh K. Heterocycles 1985, 23: 295 -
5a
Volovenko YuM.Tverdokhlebov AV.Gorulya AP.Shishkina SV.Zubatyuk RI.Shishkin OV. Eur. J. Org. Chem. 2002, 663 -
5b
Tverdokhlebov AV.Volovenko YuM.Shokol TV. Chem. Heterocycl. Compd. (Engl. Transl.) 1998, 34: 44 ; Khim. Geterotsikl. Soedin. 1998, 50 -
5c
Resnyanskaya EV.Shokol TV.Volovenko YuM.Tverdokhlebov AV. Chem. Heterocycl. Compd. (Engl. Transl.) 1999, 35: 1230 ; Khim. Geterotsikl. Soedin. 1999, 1412 -
5d
Resnyanskaya EV.Tverdokhlebov AV.Volovenko YuM.Shokol TV. Russ. J. Org. Chem. (Engl. Transl.) 2004, 40: 368 ; Zh. Org. Khim. 2004, 40, 398 -
5e
Tverdokhlebov AV.Lyashenko AB.Volovenko YuM.Tolmachev AA. Chem. Heterocycl. Compd. (Engl. Transl.) 2004, 40: 1536 ; Khim. Geterotsikl. Soedin. 2004, 1783 -
6a
Eldin AMS. Heteroat. Chem. 2003, 14: 612 -
6b
Gewald K.Hentschel M. J. Prakt. Chem. 1976, 318: 663 -
6c
Teuber H.-J.Schütz G.Erkenbrecher E. Arch. Pharm. 1980, 313: 851 -
6d
Dave CG.Shah PR.Upadhyaya SP. J. Indian Chem. Soc. 1987, 64: 713 -
6e
Dave CG.Desai ND. J. Heterocycl. Chem. 1999, 36: 729 -
7a
Volovenko YuM.Volovnenko TA.Tverdokhlebov AV.Ryabokon IG. Russ. J. Org. Chem. (Engl. Transl.) 2001, 37: 1323 ; Zh. Org. Khim. 2001, 37, 1389 -
7b
Tverdokhlebov AV.Tolmachev AA.Volovenko YuM. Collect. Czech. Chem. Commun. 2004, 69: 414 -
7c
Volovenko YuM.Resnyanska EV.Tverdokhlebov AV. Collect. Czech. Chem. Commun. 2002, 67: 356 -
7d
Volovenko YuM.Resnyanskaya EV.Tverdokhlebov AV. Chem. Heterocycl. Compd. (Engl. Transl.) 2002, 38: 324 ; Khim. Geterotsikl. Soedin. 2002, 360 -
8a
Rudnev MI.Kurbatov VP.Chub NK.Osipov OA. J. Gen. Chem. USSR (Engl. Transl.) 1988, 58: 2077 ; Zh. Obshch. Khim. 1988, 58, 2334 -
8b
Van Dormael A.Nys J. Bull. Soc. Chim. Belg. 1950, 59: 588 -
8c
Doyle FP, andKendall JD. inventors; US Patent 2542401. ; Chem. Abstr. 1951, 45, 10109 -
9a
Zakhs ER.Ponyaev AI.Subbotina MA.El’tsov AV. Russ. J. Gen. Chem. (Engl. Transl.) 2001, 71: 1076 ; Zh. Obshch. Khim. 2001, 71, 1142 -
9b
Yagupolsky LM.Kulchitsky MM.Ilchenko AYa. J. Org. Chem. USSR (Engl. Transl.) 1974, 10: 1326 ; Zh. Org. Khim. 1974, 10, 1321 -
9c
Zakhs ER.Subbotina MA.El’tsov AV. J. Org. Chem. USSR (Engl. Transl.) 1979, 15: 178 ; Zh. Org. Khim. 1979, 15, 200 - For reviews, see:
-
10a
Merour JY.Joseph B. Curr. Org. Chem. 2001, 5: 471 -
10b
Willette RE. Adv. Heterocycl. Chem. 1968, 9: 27 -
10c
Yakhontov LN.Prokopov AA. Usp. Khim. 1980, 49: 814 ; Chem. Abstr. 1980, 93, 71588 -
10d
Yakhontov LN. Usp. Khim. 1968, 37: 1258 ; Chem. Abstr. 1969, 70, 11585 -
11a
Benoit R.Dupas G.Bourguignon J.Queguiner G. Synthesis 1987, 1124 -
11b
Levacher V.Leroy C.Dupas G.Bourguignon J.Queguiner G. Synth. Commun. 1994, 24: 2697 -
11c
Brodrick A.Wibberley DG. J. Chem. Soc., Perkin Trans. 1 1975, 1910 -
11d
Monnet MO.Fauret T.Levacher V.Dupas G.Bourguignon J.Queguiner G. J. Heterocycl. Chem. 1989, 26: 1029 -
11e
Hodge CN.Aldrich PE.Wasserman ZR.Fernandez CH.Nemeth GA.Arvanitis A.Cheeseman RS.Chorvat RJ.Ciganek E.Christos TE.Gilligan PJ.Krenitsky P.Scholfield E.Strucely P. J. Med. Chem. 1999, 42: 819 -
12a
Vishwakarma LC.Sowell JW. J. Heterocycl. Chem. 1985, 22: 1429 -
12b
Toja E.Tarzia G.Ferrari P.Tuan G. J. Heterocycl. Chem. 1986, 23: 1555 -
12c
Abdelhamid AO.Abdel-Galil FM.Saleh SS. Heterocycles 1988, 27: 1861 - 13
Kiprianov AI.Pazenko ZN. Zh. Obshch. Khim. 1949, 19: 1521 ; Chem. Abstr. 1950, 44, 1097