Synthesis of a novel class of steroidal tetrazolo[1,5-a]pyridines via intramolecular 1,3-dipolar cycloadditions

被引：21

作者：

Gogoi, Junali ^{[1
]}

Bezbaruah, Pranjal ^{[1
]}

Saikia, Pallabi ^{[1
]}

Goswami, Jonalee ^{[1
]}

Gogoi, Pranjal ^{[1
]}

Boruah, Romesh Chandra ^{[1
]}

机构：

[1] CSIR NE Inst Sci & Technol, Div Med Chem, Jorhat 785006, Assam, India

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 12期

关键词：

Azasteroid; Tetrazolopyridine; Cycloaddition; Chloroformylation; ONE-POT SYNTHESIS; A-RING; FACILE SYNTHESIS; PYRAZOLES; AZIDE; DERIVATIVES;

D O I：

10.1016/j.tetlet.2012.01.050

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of a novel class of steroidal A/B/D-ring annulated tetrazolo[1,5-a]pyridine derivatives has been accomplished via intramolecular 1,3-dipolar cycloaddition reaction of azide with nitrile in aprotic solvent. The synthesis of D-ring annulated tetrazolo[1,5-a]pyridine in alcohol showed incorporation of an alcohol molecule into the heterocyclic system. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1497 / 1500

页数：4

共 35 条

[1] STEROIDAL HETEROCYCLES .X. STEROIDAL(3,2-D)PYRIMIDINES + RELATED COMPOUNDS [J].

ACKERMAN, JH ;

POTTS, GO ;

BEYLER, AL ;

CLINTON, RO .

JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (02) :238-&

[2] NEW STEROIDAL HETEROCYCLES - SYNTHESIS AND STRUCTURE OF ANDROST-2-ENO[2,3-G](TETRAZOLO[1,5-A]PYRIDIMINES), ANDROST-4-ENO[3,2-F](TETRAZOLO[1,5-A]PYRIMIDINE), AND ANDROSTANO[17,16-F](TETRAZOLO[1,5-A]PYRIMIDINES) [J].

BAJWA, JS ;

SYKES, PJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (04) :1019-1024

[3] A convenient strategy for the annulation of aryl scaffold to A/B-ring steroids under microwave irradiation [J].

Barthakur, Madan G. ;

Hasib, Abdul ;

Gogoi, Junali ;

Boruah, Romesh C. .

STEROIDS, 2010, 75 (06) :445-449

[4] A novel three-component reaction: Synthesis of some complex annelated quinolines from simple acetanilides and via intramolecular 1,3-dipolar cycloaddition of azide to nitrile [J].

Baruah, Biswajita ;

Deb, Mohit L. ;

Bhuyan, Pulak J. .

SYNLETT, 2007, (12) :1873-1876

[5] Microwave promoted one-pot synthesis of novel A-ring fused steroidal dehydropiperazines [J].

Borthakur, Moyurima ;

Barthakur, Madan G. ;

Boruah, Romesh C. .

STEROIDS, 2008, 73 (05) :539-542

[6] NOVEL PHARMACOLOGICAL ACTIVITY OF A SERIES OF SUBSTITUTED PYRIDINES [J].

BUTLER, DE ;

BASS, P ;

NORDIN, IC ;

HAUCK, FP ;

LITALIEN, YJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1971, 14 (07) :575-&

[7] Fused Tetrazoles as Azide Surrogates in Click Reaction: Efficient Synthesis of N-Heterocycle-Substituted 1,2,3-Triazoles [J].

Chattopadhyay, Buddhadeb ;

Vera, Claudia I. Rivera ;

Chuprakov, Stepan ;

Gevorgyan, Vladimir .

ORGANIC LETTERS, 2010, 12 (09) :2166-2169

[8]

CHENG YS, 1980, SYNTHESIS-STUTTGART, P223

[9] STEROIDAL[2,3-D]ISOXAZOLES [J].

CLINTON, RO ;

ARNOLD, A ;

MANSON, AJ ;

STONNER, FW ;

CHRISTIANSEN, RG ;

POTTS, GO ;

BEYLER, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (01) :279-&

[10]

Elmegeed G. A, 2004, EGYPT J CHEM, V47, P579

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