One-pot synthesis of pyridines or pyrimidines by tandem oxidation-heteroannulation of propargylic alcohols

被引：54

作者：

Bagley, MC ^{[1
]}

Hughes, DD ^{[1
]}

Sabo, HM ^{[1
]}

Taylor, PH ^{[1
]}

Xiong, X ^{[1
]}

机构：

[1] Cardiff Univ, Dept Chem, Cardiff CF10 3TB, S Glam, Wales

来源：

SYNLETT | 2003年 / 10期

关键词：

heterocycles; pyridines; pyrimidines;

D O I：

10.1055/s-2003-40827

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pyridines and pyrimidines are prepared in a single step from propargylic alcohols by in situ oxidation with o-iodoxybenzoic acid or manganese dioxide and reaction with enamines or amidines, respectively, under either thermal or microwave-assisted conditions in a new one-pot tandem oxidation-heteroannulation procedure. The reaction of a beta-ketoester, propargylic alcohol and ammonium acetate, with in situ oxidation, constitutes a highly facile three-component reaction for the synthesis of pyridines that accomplishes four distinct synthetic operations in one-pot, good yield and with total regiocontrol.

引用

页码：1443 / 1446

页数：4

共 18 条

[1] Highly efficient synthesis of pyrimidines under microwave-assisted conditions [J].

Bagley, MC ;

Hughes, DD ;

Taylor, PH .

SYNLETT, 2003, (02) :259-261

[2] A new one-step synthesis of pyridines under microwave-assisted conditions [J].

Bagley, MC ;

Lunn, R ;

Xiong, X .

TETRAHEDRON LETTERS, 2002, 43 (46) :8331-8334

[3] A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines [J].

Bagley, MC ;

Dale, JW ;

Bower, J .

CHEMICAL COMMUNICATIONS, 2002, (16) :1682-1683

[4] Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction [J].

Bagley, MC ;

Brace, C ;

Dale, JW ;

Ohnesorge, M ;

Phillips, NG ;

Xiong, X ;

Bower, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14) :1663-1671

[5] Dess-Martin periodinane oxidation of alcohols in the presence of stabilized phosphorus ylides: A convenient method for the homologation of alcohols via unstable aldehydes [J].

Barrett, AGM ;

Hamprecht, D ;

Ohkubo, M .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (26) :9376-9378

[6] In situ alcohol oxidation-Wittig reactions using N-methoxy-N-methyl-2-(triphenylphosphoranylidine)acetamide:: application to the synthesis of a novel analogue of 5-oxo-eicosatetraenoic acid [J].

Blackburn, L ;

Kanno, H ;

Taylor, RJK .

TETRAHEDRON LETTERS, 2003, 44 (01) :115-118

[7]

Blackburn L, 2002, SYNLETT, P215

[8] In situ oxidation-imine formation-reduction routes from alcohols to amines [J].

Blackburn, L ;

Taylor, RJK .

ORGANIC LETTERS, 2001, 3 (11) :1637-1639

[9] Manganese dioxide can oxidise unactivated alcohols under in situ oxidation-Wittig conditions [J].

Blackburn, L ;

Wei, XD ;

Taylor, RJK .

CHEMICAL COMMUNICATIONS, 1999, (14) :1337-1338

[10] UBER EINE NEUE PYRIDINSYNTHESE [J].

BOHLMANN, F ;

RAHTZ, D .

CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10) :2265-2272

← 1 2 →