Regioselective Heteroannelation in 4-Cyanomethyl-3,5- pyridinedicarbonitriles. Synthesis of 6-Alkoxy-3-dialkylamino-1,8-diamino-2,7- naphthyridine-4-carbonitriles

Monatshefte fur Chemie

Volumn 134, Issue 7, 2003, Pages 1045-1052

  Tverdokhlebov, Anton V ^a   Resnyanska, Elizaveta V ^a   Tolmachev, Andrey A ^a   Zavada, Alexander V ^b  

^a TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

^b CHERNIHIV NATIONAL UNIVERSITY OF TECHNOLOGY   (Ukraine)

Author keywords

2,7 Naphthyridines; Alkoxides; Heterocycles; Nucleophilic substitutions; Pyridinedicarbonitriles

Indexed keywords

2 AMINO 4 (CYANOMETHYL) 6 (1 PIPERIDINYL) 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 4 (CYANOMETHYL) 6 (1 PYRROLIDINYL) 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 4 (CYANOMETHYL) 6 (4 METHYL 1 PIPERAZINYL) 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 4 (CYANOMETHYL) 6 (4 MORPHOLINYL) 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 4 (CYANOMETHYL) 6 (DIETHYLAMINO) 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 4 (CYANOMETHYL) 6 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL] 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 6 (BUTYLETHYLAMINO) 4 (CYANOMETHYL) 3,5 PYRIDINEDICARBONITRILE; 2 AMINO 6 CHLORO 4 CYANOMETHYL 3,5 PYRIDINEDICARBONITRILE; CYANIDE; NAPHTHYRIDINE DERIVATIVE; NITRILE; OXIDE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; STEREOCHEMISTRY;

EID: 0038796084     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-003-0006-4     Document Type: Article

References (52)

1. Thepenier P, Jacqueier MJ, Nuzillard JM, Massiot G, Le Men-Olivier L, Delaude C (1997) Bull Soc R Sci Liege 65: 379; Chem Abstr 126: 314805
2. Thepenier P, Jacqueier MJ, Nuzillard JM, Massiot G, Le Men-Olivier L, Delaude C (1997) Bull Soc R Sci Liege 65: 379; Chem Abstr 126: 314805
3. Delaude C, Thepenier P, Jacquier MJ, Massiot G, Le Men-Olivier L (1992) Bull Soc R Sci Liege 61: 429; Chem Abstr 119: 91171
4. Delaude C, Thepenier P, Jacquier MJ, Massiot G, Le Men-Olivier L (1992) Bull Soc R Sci Liege 61: 429; Chem Abstr 119: 91171
5. Hart NK, Johns SR, Lamberton JA (1968) Austr J Chem 21: 1321
6. Ripperger H (1978) Phytochemistry 17: 1069
7. Tiwari KP, Minocha PK, Masood M (1980) Pol J Chem 54: 857
8. Skaltsounis AL, Tillequin F, Koch M, Pusset J, Chauviere G (1987) Heterocycles 26: 599
9. Atta-ur-Rahman, Vohra II, Choudhary MI, de Silva LB, Herath WHMW, Navarante KM (1988) Planta Med 461
10. Bracher F, Mink K (1995) Liebigs Ann Chem 645
11. Paronikyan EG, Sirakanyan SN, Noravyan AS, Asatryan TO, Markaryan KZh, Aleksanyan RA (1996) Khim-farm Zh 52: 9161; Pharm Chem J (Eng Transl) 30: 365 (1996)
12. Paronikyan EG, Sirakanyan SN, Noravyan AS, Asatryan TO, Markaryan KZh, Aleksanyan RA (1996) Khim-farm Zh 52: 9161; Pharm Chem J (Eng Transl) 30: 365 (1996)
13. Paronikyan EG, Mirzoyan GV, Noravyan AS, Avakimyan DA, Ter-Zakaryan YuZ (1993) Khim-farm Zh. 11: 29; Pharm Chem J (Eng Trans.) 27: 759 (1993)
14. Paronikyan EG, Mirzoyan GV, Noravyan AS, Avakimyan DA, Ter-Zakaryan YuZ (1993) Khim-farm Zh. 11: 29; Pharm Chem J (Eng Trans.) 27: 759 (1993)
15. Kaiho T, Suzuki T, Maruyama M, Hirayama M (1989) JP 01279884; Chem Abstr 112: 198358
16. Kaiho T, Suzuki T, Maruyama M, Hirayama M (1989) JP 01279884; Chem Abstr 112: 198358
17. Paronikyan EG, Noravyan AS, Vartanyan SA (1987) Arm Khim Zh 40: 587
18. Dorokhov VA, Yagodkin AYu, Bogdanov VS, Baranin SV (1997) Izv Russ Akad Nauk, Ser Khim 5: 1079; Russ Chem Bull 46: 1041 (1997)
19. Dorokhov VA, Yagodkin AYu, Bogdanov VS, Baranin SV (1997) Izv Russ Akad Nauk, Ser Khim 5: 1079; Russ Chem Bull 46: 1041 (1997)
20. Nemazany A, Haider N (1997) J Heterocycl Chem 34: 397
21. Aggarwal V, Singh G, Ila H, Junjappa H (1982) Synthesis 214
22. El-Reedy AM, Ibrahim MKA, Hussain SM (1989) J Prakt Chem 331: 745
23. Chupp JP, Molyneaux JM (1989) J Heterocycl Chem 26: 645
24. Buysens KJ, Vandenberghe DM, Hoornaert GJ (1996) Tetrahedron 52: 9161
25. Molina P, Lorenzo A, Aller E (1992) Tetrahedron 48: 4601
26. Ueno K, Sasaki A, Kawano K, Okabe T, Kitazawa N, Takahashi K, Yamamoto N, Suzuki Y, Matsunaga M, Kubota A (1999) PCT Int Appl WO 99 18077; Chem Abstr 130: 311813
27. Ueno K, Sasaki A, Kawano K, Okabe T, Kitazawa N, Takahashi K, Yamamoto N, Suzuki Y, Matsunaga M, Kubota A (1999) PCT Int Appl WO 99 18077; Chem Abstr 130: 311813
28. Natsugari H, Ishimaru T, Doi T (1995) EP 652218; Chem Abstr 123: 256684
29. Natsugari H, Ishimaru T, Doi T (1995) EP 652218; Chem Abstr 123: 256684
30. Failli AA (1989) US 4859671; Chem Abstr 112: 77175
31. Failli AA (1989) US 4859671; Chem Abstr 112: 77175
32. Honda H, Konno F, Koda T, Matsuda H, Katori T (1988) JP 63239285; Chem Abstr 110: 135223
33. Honda H, Konno F, Koda T, Matsuda H, Katori T (1988) JP 63239285; Chem Abstr 110: 135223
34. Noravyan AS, Paronikyan EG, Vartanyan SA (1985) Khim-farm Zh 7: 790
35. Paudler WW, Kress TI (1970) Advanc Heterocycl Chem 11: 123
36. Wozniak M, Van der Plas HC (1982) Heterocycles 19: 363
37. Volovenko YuM, Shokol TV, Tverdokhlebov AV, Babichev FS (1996) Khim Geterotsikl Soedin 1000; Chem Abstr 124: 125446
38. Volovenko YuM, Shokol TV, Tverdokhlebov AV, Babichev FS (1996) Khim Geterotsikl Soedin 1000; Chem Abstr 124: 125446
39. Tverdokhlebov AV, Volovenko YuM, Shokol TV (1998) Khim Geterotsikl Soedin 50; Chem Heterocycl Cmpd (Eng Transl) 34: 44 (1998)
40. Tverdokhlebov AV, Volovenko YuM, Shokol TV (1998) Khim Geterotsikl Soedin 50; Chem Heterocycl Cmpd (Eng Transl) 34: 44 (1998)
41. Resnyanska EV, Volovenko YuM, Shokol TV, Tverdokhlebov AV (1999) Khim Geterotsikl Soedin 1412; Chem Heterocycl Cmpd (Eng Transl) 35: 1230 (1999)
42. Resnyanska EV, Volovenko YuM, Shokol TV, Tverdokhlebov AV (1999) Khim Geterotsikl Soedin 1412; Chem Heterocycl Cmpd (Eng Transl) 35: 1230 (1999)
43. Volovenko YuM, Volovnenko TA, Tverdokhlebov AV, Ryabokon IG (2001) Zh Org Khim 37: 1389; Chem Abstr 136: 386062
44. Volovenko YuM, Volovnenko TA, Tverdokhlebov AV, Ryabokon IG (2001) Zh Org Khim 37: 1389; Chem Abstr 136: 386062
45. Volovenko YuM, Resnyanska EV, Tverdokhlebov AV (2002) Khim Geterotsikl Soedin 360; Chem Heterocycl Cmpd (Eng Transl) 38: 324 (2002)
46. Volovenko YuM, Resnyanska EV, Tverdokhlebov AV (2002) Khim Geterotsikl Soedin 360; Chem Heterocycl Cmpd (Eng Transl) 38: 324 (2002)
47. Volovenko YuM, Tverdokhlebov AV, Gorulya AP, Shishkina SV, Zubatyuk RI, Shishkin OV (2002) Eur J Org Chem 663
48. Volovenko YuM, Resnyanska EV (2002) Mendeleev Commun 12: 119
49. Volovenko YuM, Resnyanska EV, Tverdokhlebov AV (2002) Collect Czech Chem Commun 67: 365
50. Atkinson JD, Johnson MC (1968) J Chem Soc (C) 1252
51. Alhaique F, Riccieri FM, Santucci E (1975) Tetrahedron Lett 173
52. Johnson F, Nasutavicus WA (1962) J Org Chem 27: 3953