CONVENIENT NOVEL SYNTHESES OF 1,1-BIS(HETEROARYL)ALKANES

被引：44

作者：

KATRITZKY, AR

XIE, LH

FAN, WQ

机构：

[1] Department of Chemistry, University of Florida, Gainesville

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 16期

关键词：

D O I：

10.1021/jo00068a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of symmetrical 1,1-bis(heteroaryl)alkanes are prepared in excellent yields from the reaction of N-(alpha-benzotriazolylalkyl)carbamate 2 (itself easily available from the condensation of benzotriazole, an aldehyde, and an alkyl carbamate) with an excess of 2-methylthiophene or 2-methylfuran. When methyl N-(alpha-benzotriazolylalkyl)carbamate 2a is treated with 1 equiv of a heterocycle, the benzo-triazolylalkyl-substituted heterocycle is formed. These intermediates react further with other heterocycles to give unsymmetrical 1, 1-bis(heteroaryl)alkanes in good yields under mild conditions.

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页码：4376 / 4381

页数：6

相关论文

共 34 条

[21] N-[1-(BENZOTRIAZOL-1-YL)ALKYL]AMIDES, VERSATILE AMIDOALKYLATION REAGENTS .4. A NEW SYNTHETIC ROUTE TO 4H-1,3-OXAZINES [J].

KATRITZKY, AR ;

PERNAK, J ;

FAN, WQ .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1992, 334 (02) :114-118

[22]

KATRITZKY AR, 1991, SYNTHESIS-STUTTGART, P868

[23] N-[1-(BENZOTRIAZOL-1-YL)ALKYL]AMIDES, VERSATILE AMIDOALKYLATION REAGENTS .5. A GENERAL AND CONVENIENT ROUTE TO N-(ALPHA-ALKOXYALKYL)AMIDES [J].

KATRITZKY, AR ;

FAN, WQ ;

BLACK, M ;

PERNAK, J .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :547-549

[24]

KATRITZKY AR, 1989, HETEROCYCLES, V28, P1121

[25] THE CHEMISTRY OF N-SUBSTITUTED BENZOTRIAZOLES .7. THE ISOMERIC COMPOSITION AND MECHANISM OF INTERCONVERSION OF SOME N-(AMINOMETHYL)BENZOTRIAZOLE DERIVATIVES [J].

KATRITZKY, AR ;

YANNAKOPOULOU, K ;

KUZMIERKIEWICZ, W ;

AURRECOECHEA, JM ;

PALENIK, GJ ;

KOZIOL, AE ;

SZCZESNIAK, M ;

SKARJUNE, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2673-2679

[26]

KATRITZKY AR, IN PRESS SYNTHESIS

[27] REDUCTION OF HETEROCYCLIC ALCOHOLS WITH SODIUM BOROHYDRIDE-TRIFLUOROACETIC ACID - PREPARATION OF BIS-HETEROCYCLIC METHANES [J].

NUTAITIS, CF ;

PATRAGNONI, R ;

GOODKIN, G ;

NEIGHBOUR, B ;

OBAZANUTAITIS, J .

ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1991, 23 (04) :403-411

[28] STUDIES ON FURAN SERIES .1. ACIDIC CONDENSATION OF ALDEHYDES WITH METHYL 2-FUROATE [J].

PENNANEN, S ;

NYMAN, G .

ACTA CHEMICA SCANDINAVICA, 1972, 26 (03) :1018-&

[29]

Raid A., 1989, SYNTHETIC COMMUN, V19, P3169

[30] Aldehyde synthesis in furan series III. Binuclear furan bodies, difuryl and difuryl-methane [J].

Reichstein, T ;

Grussner, A ;

Zschokke, H .

HELVETICA CHIMICA ACTA, 1932, 15 :1066-1074

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