scheme i. synthesis of (2) pyridine and (3) picoline from … iii: synthesis of collidines using...

CH3CH2OH H-Zeolite CH3CH2 OH2 Zeolite -H2O

CH3CH2 Zeolite

NH3

CH3CH2 NH2 H-ZeoliteCH3CH NH -H2

(1)

(2)

CH3

HNHH

O

CH3

HN

H-ZeoliteHH

OHZeolite

CH3

N

OH

H-Zeolite

CH3

N

-H2O

N

NH

-NH3

-H2

Pyridine

(3)NH

CH3

H-ZeoliteNH2

CH3

ZeoliteNH2

CH3

Zeolite

CH3

HN

NH2

CH3HN

H3C

Zeolite

CH3

HN

NH2

CH3HN

H3CZeoliteCH3

NH2H

-2NH3

N

H2C

-H2H-Zeolite

2-Picoline Scheme I. Synthesis of (2) pyridine and (3) picoline from ethanol

Electronic Supplementary Material (ESI) for Catalysis Science & TechnologyThis journal is The Royal Society of Chemistry 2012

Scheme II: Reaction mechanism for the formation of (2) 3,5-lutidine from n-propanol and (3) 2,6-lutidine from 2-propanol over zeolites.


Scheme III: Synthesis of collidines using 2-propanol over zeolites

Scheme IV: possible reaction mechanism for the formation of 3,5-dipropyl pyridine over zeolite catalysts


Scheme V: A possible zeolite catalyzed reaction mechanism for the formation of 5-ethyl-2-methyl pyridine.

(i)

(ii)

(iii)

N

CH3

NH3

CH3

H

Zeolite-

+

N

CH3

CH3 H

+ HZeoliteN

CH3

CH3

Zeolite

+

CH3 H

O+ HZeolite

CH3 H

OH

Zeolite-

CH3 H

OH

NH3 +

Zeolite-

CH3 H

OH

NH2

+ HZeolite

CH3 H

OH2

NHH

Zeolite-

HCH3

NH

+

++HZeolite H2O

HCH3

NH+ HZeolite

HCH3

NH2 +

Zeolite- H

NH

HH

H+ CH3 CHNH2

CH2 CH NH + HZeolite

CH3 CH

NH2CH2 CH NH2

H

NH

HH

H+

+

NH2

CH NHCH3

NH2

NH2

CH NHCH3

NH2H

H

NH2

CHCH3

NH2

NH2

H

..NH2

CH NH2CH3

NH2H

+

-+

HCH3

NH2 +

Zeolite-

NH2

CH NH2CH3

NH2H CH

CH3

NH2

+

-

..NCH3

NH2H CH

CH3

NH2

H H

NH2

Zeolite-

+NCH3

NH2H CH

CH3

NH2

H

NH3

Zeolite-

N

CH3

NH2

CH3

NH2

+ HZeolite

-NH3

N

CH3

NH2

CH3

NH3

H

H

Zeolite-

+

NH3..

N

CH3

NH2

CH3

+ HZeolite-NH3

Zeolite-

+


Scheme VI: Zeolite catalyzed synthesis of 2-ethyl-3,5-dimethyl pyridine


H2COH

NH 3

(O)

H2CNH2

H2CH

O

-H2

NH3(1)

H2CNH

CH3

O

NH 3

-H2O

CH3

NH

CH2

NH

CH2

H-Zeolite-H2

Zeolite

NH NH H-Zeolite-H2, -NH3N

(2)

H2CNH

(3) CH2

HN

CH2

NH

-NH3, -H2

N

CH3

2-Phenyl pyridine

3-Picoline Scheme VII: Possible reaction mechanism for the formation of 2-phenyl pyridine and 3-picoline


Scheme VIII: Reaction mechanism for the synthesis of N-methylpyrrolidine and tetrahydrofuran


Scheme IX: Zeolite catalysed reaction mechanism for the formation of 3,4 -dihydropyrimidin-2(1H)-ones.


Scheme X: Zeolite catalysed synthesis of 1,4-diazabicyclo (2.2.2) octane and formation of pyrazine


Scheme XI: Zeolite catalyzed possible reaction mechanism for the synthesis of N,N-dimethylpiperazine.

Scheme XII: Synthesis of N-methylpiperazine over zeolite catalysts.


Scheme XIII: Synthesis of pyrrole, pyrrolidine and THF using 1,4-butane diol over zeolite catalysts.

Scheme XIV: Synthesis of piperazine and pyrazine over zeolite catalysts


Scheme XV: Possible zeolite catalyzed synthesis of annelated pyridines.


2

Scheme XVI: Possible reaction mechanism for the synthesis of isoquionline over zeolite catalysts


I

NHCOCH3

Pd-Zeolite

Pd-HZeolite

NHCOCH3

I Ph

H

Pd-HZeolite

NHCOCH3

Ph

NHCOCH3

Ph

Pd-HZeoliteNHCOCH3

Ph

NH2COCH3

Ph

Pd-HZeolite-HI

-Pd-HZeolite

NPh

COCH3

Pd-HZeoliteAq. NH4Cl

NH

Ph

2-Phenylindole Scheme XVII: Possible mechanism for the synthesis of 2-phenylindole over Pd-modified zeolites.


Scheme XVIII: Zeolite catalyzed mechanism for the formation of bis(indolyl) methanes.

Scheme XIX: Possible reaction mechanism for synthesis of N-methyl-2-pyrrolidone over zeolites.


Scheme XX: Possible reaction mechanism for the formation of 2-methylquinoxaline over zeolite.

Scheme XXI: Synthesis of 2MEQ and 4MEQ over zeolites.


NH2

O H-Zeolite OH Zeolite OH H-Zeolite

OH2 Zeolite-H2O

Zeolite

N

N

(1)

4-Methyl quinoline

NH2(2)

H-Zeolite

N

-H2

2-Methyl quinoline

N

-H2

Zeolite

NH2

Zeolite

H

NH2

H

H

H

H-Zeolite

H

Scheme XXII: Synthesis of 4-MEQ, 2-MEQ from crotonaldehyde and aniline.


Scheme XXIII: Vapor phase alkylation of indole with methanol over zeolites.


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scheme i. synthesis of (2) pyridine and (3) picoline from … iii: synthesis of collidines using...

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