SCOPUS 정보 검색 플랫폼

Volumn 2, Issue 1, 2005, Pages 18-20

First efficient one-pot synthesis of tetrahydropyrrolo[2,3-d]azocines and tetrahydroazocino[4,5-b]indoles

Author keywords

Azocines; Carbolines; Pyrroles; Ring expansion; Tandem cleavage

Indexed keywords

EID: 30344433585 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/1570178053400090 Document Type: Review

Times cited : (18)

References (13)

1
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- (1999) Tetrahedron , vol.55 , pp. 3117
- Bennasar, M.-L.¹ Zulaica, E.² Ramirez, A.³ Bosch, J.⁴

2
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- b) Bertha, C. M.; Ellis, M.; Flippen-Anderson, J. L.; Porreca, F.; Rothman, R.B.; Davis, P.; Xu, H.; Becketts, K.; Rice, K.C. J. Med. Chem., 1996, 39, 2081.
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- Bertha, C.M.¹ Ellis, M.² Flippen-Anderson, J.L.³ Porreca, F.⁴ Rothman, R.B.⁵ Davis, P.⁶ Xu, H.⁷ Becketts, K.⁸ Rice, K.C.⁹

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- c) Alazard, J.-P.; Millet-Paillusson, C.; Guenard, D.; Thal, C. B. Soc. Chim. Fr., 1996, 133, 251.
- (1996) B. Soc. Chim. Fr , vol.133 , pp. 251
- Alazard, J.-P.¹ Millet-Paillusson, C.² Guenard, D.³ Thal, C.⁴

4
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- Reviews: a Alvarez, M.; Joule, John A. Chemistry of Heterocyclic Compounds (Chichester, United Kingdom), 1994, 25, 261.
- Reviews: a) Alvarez, M.; Joule, John A. Chemistry of Heterocyclic Compounds (Chichester, United Kingdom), 1994, 25, 261.

5
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- b) Alvarez M.; Joule J.A. Alkaloids, 2001, 57, 235.
- (2001) Alkaloids , vol.57 , pp. 235
- Alvarez, M.¹ Joule, J.A.²

6
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- Bosch, J.; Mauleon, D.; Boncompte, F.; Ganados, R. J.Heterocyclic Chem., 1981, 18, 263.
- (1981) J.Heterocyclic Chem , vol.18 , pp. 263
- Bosch, J.¹ Mauleon, D.² Boncompte, F.³ Ganados, R.⁴

7
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- Varlamov, A.V.; Borisova, T.N.; Voskressensky, L.G.; Kulikova, L.N.; Soklakova, T.A.; Chernyshev, A.I.; Alexandrov, G.C. Tetrahedron Lett., 2002, 43, 6767.
- (2002) Tetrahedron Lett , vol.43 , pp. 6767
- Varlamov, A.V.¹ Borisova, T.N.² Voskressensky, L.G.³ Kulikova, L.N.⁴ Soklakova, T.A.⁵ Chernyshev, A.I.⁶ Alexandrov, G.C.⁷

8
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- For the review on THPP synthesis see
- a) For the review on THPP synthesis see: Varlamov, A.V.; Borisova, T.N.; Voskressensky, L.G. Synthesis, 2002, 2, 155.
- (2002) Synthesis , vol.2 , pp. 155
- Varlamov, A.V.¹ Borisova, T.N.² Voskressensky, L.G.³

9
- 0347033231
- For the synthesis of the THPPs 1a-f see: Voskressensky, L.G.; de Candia, M.; Carotti, A.; Borisova,T.N.; Kulikova, L.N.; Varlamov, A.V.; Altomare, C. J.Pharm.Pharmacol., 2003, 55, 323.
- b) For the synthesis of the THPPs 1a-f see: Voskressensky, L.G.; de Candia, M.; Carotti, A.; Borisova,T.N.; Kulikova, L.N.; Varlamov, A.V.; Altomare, C. J.Pharm.Pharmacol., 2003, 55, 323.

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11
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- Borisova, T.N.; Voskressensky, L.G.; Kulikova, L.N.; Soklakova, T.A.; Varlamov, A.V. Mol. Diver., 2003, 6, 207.
- (2003) Mol. Diver , vol.6 , pp. 207
- Borisova, T.N.¹ Voskressensky, L.G.² Kulikova, L.N.³ Soklakova, T.A.⁴ Varlamov, A.V.⁵

12
- 46149110423
- Experimental procedure: To a solution of 1 mmol of the THPP 1a-f or THPI 4 derivative in 5 ml of dry methanol, 1.2 mmol of DMAD or EP was added. The reaction mixture was kept at r.t. for 24 hours and the solvent was evaporated under reduced pressure. 50 μmol of trimethylsilyl triflate in 5 ml of absolute THF was added to the reaction mixture and stirring was continued for additional 24 hours. Solvent was evaporated under reduced pressure and the residue was recrystallized from ethyl acetate, hexane mixture to give target azocine derivatives 3a-f or 5. Data for 3c Colorless crystals, Mp 220-222 °C. 1H NMR (400 MHz, CDCl3, δ 9.85(bs, 1H, NH, 6.52 (d, 1H, J=2.5 Hz, H-3, 4.33 (q, 1H, J=7.4 Hz, H-4, 3.61 (s, 3H, OCH3, 3.55(s, 3H, OCH3, 3.54(m, 1H, H-8a, 3.28 (m,1H, H-9, 3.17(dd, 1H, J= 14.2, 5.6 Hz, H-8e, 2.50 (s, 3H, N-CH3, 3.20 s, 3H, COCH3, 1.2
- 5 requires C, 62.05; H, 6.94; N, 8.04.

13
- 46149104886
- Data for 5: Yellow crystals, Mp 194-196 °C. 1H NMR (400 MHz, CDCl3, δ 7.82(bs, 1H, NH, 7.48 (s, 1H, H-4, 7.32 (dd, 1H, J7H-F=9.3 Hz, J7H-9H =2.0 Hz, H-7, 7.10 (dd, 1H, J10H-9H =8.7 Hz, J10H-F =4.3 Hz, H-10, 6.8(td, 1H, J9H-F=J9H-10H, 8.7 Hz, J9H-7H=2.0 Hz, H-9, 4.18 (q, 2H, J=7.1 Hz, O-CH2, 3.99 (m, 4H,CH2-6+ CH2-2, 3.40 (spt, J=6.8 Hz, CH-iPr, 3.18 (t, 2H, J=5.5 Hz, CH2-1, 1.31 (t, 3H, J=7.1 Hz, O-CH2CH3, 1.19 (d, 6H, J= 6.8 Hz, 2×CH3, 13C NMR (100 MHz, CDCl3, 165.1 (C=O, 157.2(d, 1J C-F, 230 Hz, C-8, 147.6 (C-4, 133.8 (C-12a, 132.2 (C-10a, 124.3 (C-6b, 113.5 (C-10, 110.4 d, 2JC-F= 21 Hz, C-9
- 2 requires C, 69.07; H, 7.02; N, 8.48.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.